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2015 | OriginalPaper | Buchkapitel

Passerini and Ugi Multicomponent Reactions in Polymer Science

verfasst von : Ansgar Sehlinger, Michael A. R. Meier

Erschienen in: Multi-Component and Sequential Reactions in Polymer Synthesis

Verlag: Springer International Publishing

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Abstract

Multicomponent reactions (MCRs) include more than two starting materials and are characterized by highly atom-efficient and straightforward practical procedures. Some of the most important MCRs in organic chemistry are the isocyanide-based MCRs, namely the Passerini three-component and Ugi four-component reaction. These reactions are, for example, often applied in combinatorial and medicinal chemistry due to their easy access to diversity or for the creation of complex structural motifs in the total synthesis of natural products.
Only recently, they also gained great interest in macromolecular chemistry, since the variation of the single components displays an easy tool to adjust the properties of the polymers and facile introduction of functional groups is enabled. Hereby, tailor-made high-performance and smart materials can be obtained, which are currently highly requested for many applications. In order to attain this objective, several strategies are followed: the MCRs are used to synthesize structurally diverse monomers for subsequent polymerization, or by the use of bifunctional components, these reactions are directly utilized as polymerization method. Moreover, the Passerini and Ugi reaction are applied in macromolecular engineering as conjugation method of two kinds of polymers, or as tool for grafting reactions as well as in the creation of defined primary structures. Finally, these valuable reactions are also used in the convergent and divergent synthesis of dendritic architectures.

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Literatur
1.
Zurück zum Zitat Passerini M (1921) Gazz Chem Ital 51:126–129 Passerini M (1921) Gazz Chem Ital 51:126–129
2.
Zurück zum Zitat Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem 72(7–8):267–268CrossRef Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem 72(7–8):267–268CrossRef
3.
Zurück zum Zitat Wessjohann LA, Neves Filho RAW, Rivera DG (2012) Multiple multicomponent reactions with isocyanides. In: Isocyanide chemistry. Wiley-VCH, Weinheim, pp 233–262CrossRef Wessjohann LA, Neves Filho RAW, Rivera DG (2012) Multiple multicomponent reactions with isocyanides. In: Isocyanide chemistry. Wiley-VCH, Weinheim, pp 233–262CrossRef
4.
Zurück zum Zitat Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106(1):17–89CrossRef Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106(1):17–89CrossRef
6.
Zurück zum Zitat Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112(6):3083–3135CrossRef Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112(6):3083–3135CrossRef
7.
Zurück zum Zitat Akritopoulou-Zanze I (2008) Isocyanide-based multicomponent reactions in drug discovery. Curr Opin Chem Biol 12(3):324–331CrossRef Akritopoulou-Zanze I (2008) Isocyanide-based multicomponent reactions in drug discovery. Curr Opin Chem Biol 12(3):324–331CrossRef
8.
Zurück zum Zitat Weber L (2002) Multi-component reactions and evolutionary chemistry. Drug Discov Today 7(2):143–147CrossRef Weber L (2002) Multi-component reactions and evolutionary chemistry. Drug Discov Today 7(2):143–147CrossRef
9.
Zurück zum Zitat Dai Q, Xie X, Xu S, Ma D, Tang S, She X (2011) Total syntheses of tardioxopiperazine A, isoechinulin A, and variecolorin C. Org Lett 13(9):2302–2305CrossRef Dai Q, Xie X, Xu S, Ma D, Tang S, She X (2011) Total syntheses of tardioxopiperazine A, isoechinulin A, and variecolorin C. Org Lett 13(9):2302–2305CrossRef
10.
Zurück zum Zitat Takiguchi S, Iizuka T, Kumakura Y-s, Murasaki K, Ban N, Higuchi K, Kawasaki T (2010) Total syntheses of (−)-fructigenine A and (−)-5-N-acetylardeemin. J Org Chem 75(4):1126–1131CrossRef Takiguchi S, Iizuka T, Kumakura Y-s, Murasaki K, Ban N, Higuchi K, Kawasaki T (2010) Total syntheses of (−)-fructigenine A and (−)-5-N-acetylardeemin. J Org Chem 75(4):1126–1131CrossRef
11.
Zurück zum Zitat Falck JR, Manna S (1981) An intramolecular Passerini reaction: synthesis of hydrastine. Tetrahedron Lett 22(7):619–620CrossRef Falck JR, Manna S (1981) An intramolecular Passerini reaction: synthesis of hydrastine. Tetrahedron Lett 22(7):619–620CrossRef
12.
Zurück zum Zitat Kakuchi R (2014) Multicomponent reactions in polymer synthesis. Angew Chem Int Ed 53(1):46–48CrossRef Kakuchi R (2014) Multicomponent reactions in polymer synthesis. Angew Chem Int Ed 53(1):46–48CrossRef
13.
Zurück zum Zitat Rudick JG (2013) Innovative macromolecular syntheses via isocyanide multicomponent reactions. J Polym Sci Part A Polym Chem 51(19):3985–3991CrossRef Rudick JG (2013) Innovative macromolecular syntheses via isocyanide multicomponent reactions. J Polym Sci Part A Polym Chem 51(19):3985–3991CrossRef
14.
Zurück zum Zitat Wang S, Fu C, Wei Y, Tao L (2014) Facile one-pot synthesis of new functional polymers through multicomponent systems. Macromol Chem Phys 215(6):486–492CrossRef Wang S, Fu C, Wei Y, Tao L (2014) Facile one-pot synthesis of new functional polymers through multicomponent systems. Macromol Chem Phys 215(6):486–492CrossRef
15.
Zurück zum Zitat Rubinshtein M, James CR, Young JL, Ma YJ, Kobayashi Y, Gianneschi NC, Yang J (2010) Facile procedure for generating side chain functionalized poly(α-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation. Org Lett 12(15):3560–3563CrossRef Rubinshtein M, James CR, Young JL, Ma YJ, Kobayashi Y, Gianneschi NC, Yang J (2010) Facile procedure for generating side chain functionalized poly(α-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation. Org Lett 12(15):3560–3563CrossRef
16.
Zurück zum Zitat Kreye O, Tóth T, Meier MAR (2011) Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers. J Am Chem Soc 133(6):1790–1792CrossRef Kreye O, Tóth T, Meier MAR (2011) Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers. J Am Chem Soc 133(6):1790–1792CrossRef
17.
Zurück zum Zitat Mutlu H, de Espinosa LM, Meier MAR (2011) Acyclic diene metathesis: a versatile tool for the construction of defined polymer architectures. Chem Soc Rev 40(3):1404–1445CrossRef Mutlu H, de Espinosa LM, Meier MAR (2011) Acyclic diene metathesis: a versatile tool for the construction of defined polymer architectures. Chem Soc Rev 40(3):1404–1445CrossRef
18.
Zurück zum Zitat Atallah P, Wagener KB, Schulz MD (2013) ADMET: the future revealed. Macromolecules 46(12):4735–4741CrossRef Atallah P, Wagener KB, Schulz MD (2013) ADMET: the future revealed. Macromolecules 46(12):4735–4741CrossRef
19.
Zurück zum Zitat Simocko C, Atallah P, Wagener KB (2013) A brief examination of the latest ADMET chemistry. Curr Org Chem 17(22):2749–2763CrossRef Simocko C, Atallah P, Wagener KB (2013) A brief examination of the latest ADMET chemistry. Curr Org Chem 17(22):2749–2763CrossRef
20.
Zurück zum Zitat Mutlu H, Meier MAR (2010) Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol 112(1):10–30CrossRef Mutlu H, Meier MAR (2010) Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol 112(1):10–30CrossRef
21.
Zurück zum Zitat Kolb N, Meier MAR (2013) Grafting onto a renewable unsaturated polyester via thiol–ene chemistry and cross-metathesis. Eur Polym J 49(4):843–852CrossRef Kolb N, Meier MAR (2013) Grafting onto a renewable unsaturated polyester via thiol–ene chemistry and cross-metathesis. Eur Polym J 49(4):843–852CrossRef
22.
Zurück zum Zitat Kreye O, Trefzger C, Sehlinger A, Meier MAR (2014) Multicomponent reactions with a convertible isocyanide: efficient and versatile grafting of ADMET-derived polymers. Macromol Chem Phys 215(22):2207–2220 Kreye O, Trefzger C, Sehlinger A, Meier MAR (2014) Multicomponent reactions with a convertible isocyanide: efficient and versatile grafting of ADMET-derived polymers. Macromol Chem Phys 215(22):2207–2220
23.
Zurück zum Zitat Sehlinger A, Kreye O, Meier MAR (2013) Tunable polymers obtained from Passerini multicomponent reaction derived acrylate monomers. Macromolecules 46(15):6031–6037CrossRef Sehlinger A, Kreye O, Meier MAR (2013) Tunable polymers obtained from Passerini multicomponent reaction derived acrylate monomers. Macromolecules 46(15):6031–6037CrossRef
24.
Zurück zum Zitat Sehlinger A, de Espinosa LM, Meier MAR (2013) Synthesis of diverse asymmetric α,ω-dienes via the Passerini three-component reaction for head-to-tail ADMET polymerization. Macromol Chem Phys 214(24):2821–2828CrossRef Sehlinger A, de Espinosa LM, Meier MAR (2013) Synthesis of diverse asymmetric α,ω-dienes via the Passerini three-component reaction for head-to-tail ADMET polymerization. Macromol Chem Phys 214(24):2821–2828CrossRef
25.
Zurück zum Zitat Montero de Espinosa M, Meier MAR (2011) Synthesis of star- and block-copolymers using ADMET: head-to-tail selectivity during step-growth polymerization. Chem Commun 47(6):1908–1910CrossRef Montero de Espinosa M, Meier MAR (2011) Synthesis of star- and block-copolymers using ADMET: head-to-tail selectivity during step-growth polymerization. Chem Commun 47(6):1908–1910CrossRef
26.
Zurück zum Zitat Chatterjee AK, Choi T-L, Sanders DP, Grubbs RH (2003) A general model for selectivity in olefin cross metathesis. J Am Chem Soc 125(37):11360–11370CrossRef Chatterjee AK, Choi T-L, Sanders DP, Grubbs RH (2003) A general model for selectivity in olefin cross metathesis. J Am Chem Soc 125(37):11360–11370CrossRef
27.
Zurück zum Zitat Demel S, Slugovc C, Stelzer F, Fodor-Csorba K, Galli G (2003) Alternating diene metathesis polycondensation (ALTMET) – a versatile tool for the preparation of perfectly alternating AB copolymers. Macromol Rapid Commun 24(10):636–641CrossRef Demel S, Slugovc C, Stelzer F, Fodor-Csorba K, Galli G (2003) Alternating diene metathesis polycondensation (ALTMET) – a versatile tool for the preparation of perfectly alternating AB copolymers. Macromol Rapid Commun 24(10):636–641CrossRef
28.
Zurück zum Zitat Pirrung MC, Sarma KD (2003) Multicomponent reactions are accelerated in water. J Am Chem Soc 126(2):444–445CrossRef Pirrung MC, Sarma KD (2003) Multicomponent reactions are accelerated in water. J Am Chem Soc 126(2):444–445CrossRef
29.
Zurück zum Zitat Schmidt S, Koldevitz M, Noy J-M, Roth PJ (2015) Multicomponent isocyanide-based synthesis of reactive styrenic and (meth)acrylic monomers and their RAFT (co)polymerization. Polym Chem 6:44–54 Schmidt S, Koldevitz M, Noy J-M, Roth PJ (2015) Multicomponent isocyanide-based synthesis of reactive styrenic and (meth)acrylic monomers and their RAFT (co)polymerization. Polym Chem 6:44–54
30.
Zurück zum Zitat Noy J-M, Koldevitz M, Roth PJ (2015) Thiol-reactive functional poly(meth)acrylates: multicomponent monomer synthesis, RAFT (co)polymerization and highly efficient thiol-para-fluoro postpolymerization modification. Polym Chem 6:436–447 Noy J-M, Koldevitz M, Roth PJ (2015) Thiol-reactive functional poly(meth)acrylates: multicomponent monomer synthesis, RAFT (co)polymerization and highly efficient thiol-para-fluoro postpolymerization modification. Polym Chem 6:436–447
31.
Zurück zum Zitat Leon F, Rivera DG, Wessjohann LA (2008) Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions. J Org Chem 73(5):1762–1767CrossRef Leon F, Rivera DG, Wessjohann LA (2008) Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions. J Org Chem 73(5):1762–1767CrossRef
32.
Zurück zum Zitat Deng X-X, Li L, Li Z-L, Lv A, Du F-S, Li Z-C (2012) Sequence regulated poly(ester-amide)s based on Passerini reaction. ACS Macro Lett 1(11):1300–1303CrossRef Deng X-X, Li L, Li Z-L, Lv A, Du F-S, Li Z-C (2012) Sequence regulated poly(ester-amide)s based on Passerini reaction. ACS Macro Lett 1(11):1300–1303CrossRef
33.
Zurück zum Zitat Kan X-W, Deng X-X, Du F-S, Li Z-C (2015) Concurrent oxidation of alcohols and the Passerini three-component polymerization for the synthesis of functional poly(ester amide)s. Macromol Chem Phys 215(22): 2221–2228 Kan X-W, Deng X-X, Du F-S, Li Z-C (2015) Concurrent oxidation of alcohols and the Passerini three-component polymerization for the synthesis of functional poly(ester amide)s. Macromol Chem Phys 215(22): 2221–2228
34.
Zurück zum Zitat Ngouansavanh T, Zhu J (2006) Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of O-iodoxybenzoic acid. Angew Chem Int Ed 45(21):3495–3497CrossRef Ngouansavanh T, Zhu J (2006) Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of O-iodoxybenzoic acid. Angew Chem Int Ed 45(21):3495–3497CrossRef
35.
Zurück zum Zitat Wang Y-Z, Deng X-X, Li L, Li Z-L, Du F-S, Li Z-C (2013) One-pot synthesis of polyamides with various functional side groups via Passerini reaction. Polym Chem 4(3):444–448CrossRef Wang Y-Z, Deng X-X, Li L, Li Z-L, Du F-S, Li Z-C (2013) One-pot synthesis of polyamides with various functional side groups via Passerini reaction. Polym Chem 4(3):444–448CrossRef
36.
Zurück zum Zitat Obrecht R, Herrmann R, Ugi I (1985) Isocyanide synthesis with phosphoryl chloride and diisopropylamine. Synthesis 1985(04):400–402CrossRef Obrecht R, Herrmann R, Ugi I (1985) Isocyanide synthesis with phosphoryl chloride and diisopropylamine. Synthesis 1985(04):400–402CrossRef
37.
Zurück zum Zitat Ugi I, Fetzer U, Eholzer U, Knupfer H, Offermann K (1965) Isonitrile syntheses. Angew Chem Int Ed Engl 4(6):472–484CrossRef Ugi I, Fetzer U, Eholzer U, Knupfer H, Offermann K (1965) Isonitrile syntheses. Angew Chem Int Ed Engl 4(6):472–484CrossRef
38.
Zurück zum Zitat Sehlinger A, Schneider R, Meier MAR (2014) Passerini addition polymerization of an AB-type monomer – a convenient route to versatile polyesters. Eur Polym J 50:150–157CrossRef Sehlinger A, Schneider R, Meier MAR (2014) Passerini addition polymerization of an AB-type monomer – a convenient route to versatile polyesters. Eur Polym J 50:150–157CrossRef
39.
Zurück zum Zitat Zhang L-J, Deng X-X, Du F-S, Li Z-C (2013) Chemical synthesis of functional poly(4-hydroxybutyrate) with controlled degradation via intramolecular cyclization. Macromolecules 46(24):9554–9562CrossRef Zhang L-J, Deng X-X, Du F-S, Li Z-C (2013) Chemical synthesis of functional poly(4-hydroxybutyrate) with controlled degradation via intramolecular cyclization. Macromolecules 46(24):9554–9562CrossRef
40.
Zurück zum Zitat Deng X-X, Cui Y, Du F-S, Li Z-C (2014) Functional highly branched polymers from multicomponent polymerization (MCP) based on the ABC type Passerini reaction. Polym Chem 5(10):3316–3320CrossRef Deng X-X, Cui Y, Du F-S, Li Z-C (2014) Functional highly branched polymers from multicomponent polymerization (MCP) based on the ABC type Passerini reaction. Polym Chem 5(10):3316–3320CrossRef
41.
Zurück zum Zitat de Nooy AEJ, Capitani D, Masci G, Crescenzi V (2000) Ionic polysaccharide hydrogels via the Passerini and Ugi multicomponent condensations: synthesis, behavior and solid-state NMR characterization. Biomacromolecules 1(2):259–267CrossRef de Nooy AEJ, Capitani D, Masci G, Crescenzi V (2000) Ionic polysaccharide hydrogels via the Passerini and Ugi multicomponent condensations: synthesis, behavior and solid-state NMR characterization. Biomacromolecules 1(2):259–267CrossRef
42.
Zurück zum Zitat de Nooy AEJ, Masci G, Crescenzi V (1999) Versatile synthesis of polysaccharide hydrogels using the Passerini and Ugi multicomponent condensations. Macromolecules 32(4):1318–1320CrossRef de Nooy AEJ, Masci G, Crescenzi V (1999) Versatile synthesis of polysaccharide hydrogels using the Passerini and Ugi multicomponent condensations. Macromolecules 32(4):1318–1320CrossRef
43.
Zurück zum Zitat Li L, Lv A, Deng X-X, Du F-S, Li Z-C (2013) Facile synthesis of photo-cleavable polymers via Passerini reaction. Chem Commun 49(76):8549–8551CrossRef Li L, Lv A, Deng X-X, Du F-S, Li Z-C (2013) Facile synthesis of photo-cleavable polymers via Passerini reaction. Chem Commun 49(76):8549–8551CrossRef
44.
Zurück zum Zitat Li L, Deng X-X, Li Z-L, Du F-S, Li Z-C (2014) Multifunctional photodegradable polymers for reactive micropatterns. Macromolecules 47(14):4660–4667CrossRef Li L, Deng X-X, Li Z-L, Du F-S, Li Z-C (2014) Multifunctional photodegradable polymers for reactive micropatterns. Macromolecules 47(14):4660–4667CrossRef
45.
Zurück zum Zitat Lin W, Sun T, Zheng M, Xie Z, Huang Y, Jing X (2014) Synthesis of cross-linked polymers via multi-component Passerini reaction and their application as efficient photocatalysts. RSC Adv 4(48):25114–25117CrossRef Lin W, Sun T, Zheng M, Xie Z, Huang Y, Jing X (2014) Synthesis of cross-linked polymers via multi-component Passerini reaction and their application as efficient photocatalysts. RSC Adv 4(48):25114–25117CrossRef
46.
Zurück zum Zitat Wang S, Zhang N, Ge X, Wan Y, Li X, Yan L, Xia Y, Song B (2014) Self-assembly of an azobenzene-containing polymer prepared by a multi-component reaction: supramolecular nanospheres with photo-induced deformation properties. Soft Matter 10(27):4833–4839CrossRef Wang S, Zhang N, Ge X, Wan Y, Li X, Yan L, Xia Y, Song B (2014) Self-assembly of an azobenzene-containing polymer prepared by a multi-component reaction: supramolecular nanospheres with photo-induced deformation properties. Soft Matter 10(27):4833–4839CrossRef
47.
Zurück zum Zitat Li L, Kan X-W, Deng X-X, Song C-C, Du F-S, Li Z-C (2013) Simultaneous dual end-functionalization of PEG via the Passerini three-component reaction for the synthesis of ABC miktoarm terpolymers. J Polym Sci Part A Polym Chem 51(4):865–873CrossRef Li L, Kan X-W, Deng X-X, Song C-C, Du F-S, Li Z-C (2013) Simultaneous dual end-functionalization of PEG via the Passerini three-component reaction for the synthesis of ABC miktoarm terpolymers. J Polym Sci Part A Polym Chem 51(4):865–873CrossRef
48.
Zurück zum Zitat Deng X-X, Cui Y, Wang Y-Z, Du F-S, Li Z-C (2014) Graft copolymers with polyamide backbones via combination of Passerini multicomponent polymerization and controlled chain-growth polymerization. Aust J Chem 67(4):555–561CrossRef Deng X-X, Cui Y, Wang Y-Z, Du F-S, Li Z-C (2014) Graft copolymers with polyamide backbones via combination of Passerini multicomponent polymerization and controlled chain-growth polymerization. Aust J Chem 67(4):555–561CrossRef
49.
Zurück zum Zitat Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85(14):2149–2154CrossRef Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85(14):2149–2154CrossRef
50.
Zurück zum Zitat Espeel P, Carrette LLG, Bury K, Capenberghs S, Martins JC, Du Prez FE, Madder A (2013) Multifunctionalized sequence-defined oligomers from a single building block. Angew Chem Int Ed 52(50):13261–13264CrossRef Espeel P, Carrette LLG, Bury K, Capenberghs S, Martins JC, Du Prez FE, Madder A (2013) Multifunctionalized sequence-defined oligomers from a single building block. Angew Chem Int Ed 52(50):13261–13264CrossRef
51.
Zurück zum Zitat Li X, Liu DR (2004) DNA-templated organic synthesis: nature’s strategy for controlling chemical reactivity applied to synthetic molecules. Angew Chem Int Ed 43(37):4848–4870CrossRef Li X, Liu DR (2004) DNA-templated organic synthesis: nature’s strategy for controlling chemical reactivity applied to synthetic molecules. Angew Chem Int Ed 43(37):4848–4870CrossRef
52.
Zurück zum Zitat Lutz J-F, Ouchi M, Liu DR, Sawamoto M (2013) Sequence-controlled polymers. Science 341:6146CrossRef Lutz J-F, Ouchi M, Liu DR, Sawamoto M (2013) Sequence-controlled polymers. Science 341:6146CrossRef
53.
Zurück zum Zitat Lv A, Deng X-X, Li L, Li Z-L, Wang Y-Z, Du F-S, Li Z-C (2013) Facile synthesis of multi-block copolymers containing poly(ester-amide) segments with an ordered side group sequence. Polym Chem 4(13):3659–3662CrossRef Lv A, Deng X-X, Li L, Li Z-L, Wang Y-Z, Du F-S, Li Z-C (2013) Facile synthesis of multi-block copolymers containing poly(ester-amide) segments with an ordered side group sequence. Polym Chem 4(13):3659–3662CrossRef
54.
Zurück zum Zitat Solleder SC, Meier MAR (2014) Sequence control in polymer chemistry through the Passerini three-component reaction. Angew Chem Int Ed 53(3):711–714CrossRef Solleder SC, Meier MAR (2014) Sequence control in polymer chemistry through the Passerini three-component reaction. Angew Chem Int Ed 53(3):711–714CrossRef
55.
Zurück zum Zitat Sowinska M, Urbanczyk-Lipkowska Z (2014) Advances in the chemistry of dendrimers. New J Chem 38(6):2168–2203CrossRef Sowinska M, Urbanczyk-Lipkowska Z (2014) Advances in the chemistry of dendrimers. New J Chem 38(6):2168–2203CrossRef
56.
Zurück zum Zitat Jee J-A, Spagnuolo LA, Rudick JG (2012) Convergent synthesis of dendrimers via the Passerini three-component reaction. Org Lett 14(13):3292–3295CrossRef Jee J-A, Spagnuolo LA, Rudick JG (2012) Convergent synthesis of dendrimers via the Passerini three-component reaction. Org Lett 14(13):3292–3295CrossRef
57.
Zurück zum Zitat Wessjohann LA, Henze M, Kreye O, Rivera DG (2011) MCR dendrimers. Patent WO 2011/134607 Wessjohann LA, Henze M, Kreye O, Rivera DG (2011) MCR dendrimers. Patent WO 2011/134607
58.
Zurück zum Zitat Wessjohann LA, Henze M, Kreye O, Rivera DG (2013) MCR dendrimers. European Patent EP 2563847 Wessjohann LA, Henze M, Kreye O, Rivera DG (2013) MCR dendrimers. European Patent EP 2563847
59.
Zurück zum Zitat Kreye O, Kugele D, Faust L, Meier MAR (2014) Divergent dendrimer synthesis via the Passerini three-component reaction and olefin cross-metathesis. Macromol Rapid Commun 35(3):317–322CrossRef Kreye O, Kugele D, Faust L, Meier MAR (2014) Divergent dendrimer synthesis via the Passerini three-component reaction and olefin cross-metathesis. Macromol Rapid Commun 35(3):317–322CrossRef
60.
Zurück zum Zitat Deng X-X, Du F-S, Li Z-C (2014) Combination of orthogonal ABB and ABC multicomponent reactions toward efficient divergent synthesis of dendrimers with structural diversity. ACS Macro Lett 3(7):667–670CrossRef Deng X-X, Du F-S, Li Z-C (2014) Combination of orthogonal ABB and ABC multicomponent reactions toward efficient divergent synthesis of dendrimers with structural diversity. ACS Macro Lett 3(7):667–670CrossRef
61.
Zurück zum Zitat Robotham C, Baker C, Cuevas B, Abboud K, Wright D (2003) A multi-component reaction (MCR) approach to the synthesis of highly diverse polymers with polypeptide-like features. Mol Diversity 6(3–4):237–244 Robotham C, Baker C, Cuevas B, Abboud K, Wright D (2003) A multi-component reaction (MCR) approach to the synthesis of highly diverse polymers with polypeptide-like features. Mol Diversity 6(3–4):237–244
62.
Zurück zum Zitat Kreye O, Türünç O, Sehlinger A, Rackwitz J, Meier MAR (2012) Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction. Chem-Eur J 18(18):5767–5776CrossRef Kreye O, Türünç O, Sehlinger A, Rackwitz J, Meier MAR (2012) Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction. Chem-Eur J 18(18):5767–5776CrossRef
63.
Zurück zum Zitat Keating TA, Armstrong RW (1998) The Ugi five-component condensation using CO2, CS2, and COS as oxidized carbon sources. J Org Chem 63(3):867–871CrossRef Keating TA, Armstrong RW (1998) The Ugi five-component condensation using CO2, CS2, and COS as oxidized carbon sources. J Org Chem 63(3):867–871CrossRef
64.
Zurück zum Zitat Sehlinger A, Schneider R, Meier MAR (2014) Ugi reactions with CO2: access to functionalized polyurethanes, polycarbonates, polyamides, and polyhydantoins. Macromol Rapid Commun 35(21):1866–1871 Sehlinger A, Schneider R, Meier MAR (2014) Ugi reactions with CO2: access to functionalized polyurethanes, polycarbonates, polyamides, and polyhydantoins. Macromol Rapid Commun 35(21):1866–1871
65.
Zurück zum Zitat Hulme C, Ma L, Romano JJ, Morton G, Tang S-Y, Cherrier M-P, Choi S, Salvino J, Labaudiniere R (2000) Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction. Tetrahedron Lett 41(12):1889–1893CrossRef Hulme C, Ma L, Romano JJ, Morton G, Tang S-Y, Cherrier M-P, Choi S, Salvino J, Labaudiniere R (2000) Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction. Tetrahedron Lett 41(12):1889–1893CrossRef
66.
Zurück zum Zitat Wessjohann LA, Rivera DG, León F (2007) Freezing Imine exchange in dynamic combinatorial libraries with Ugi reactions: versatile access to templated macrocycles. Org Lett 9(23):4733–4736CrossRef Wessjohann LA, Rivera DG, León F (2007) Freezing Imine exchange in dynamic combinatorial libraries with Ugi reactions: versatile access to templated macrocycles. Org Lett 9(23):4733–4736CrossRef
67.
Zurück zum Zitat Wessjohann LA, Rivera DG, Vercillo OE (2009) Multiple multicomponent macrocyclizations (MiBs): a strategic development toward macrocycle diversity. Chem Rev 109(2):796–814CrossRef Wessjohann LA, Rivera DG, Vercillo OE (2009) Multiple multicomponent macrocyclizations (MiBs): a strategic development toward macrocycle diversity. Chem Rev 109(2):796–814CrossRef
68.
Zurück zum Zitat Crescenzi V, Francescangeli A, Capitani D, Mannina L, Renier D, Bellini D (2003) Hyaluronan networking via Ugi’s condensation using lysine as cross-linker diamine. Carbohydr Polym 53(3):311–316CrossRef Crescenzi V, Francescangeli A, Capitani D, Mannina L, Renier D, Bellini D (2003) Hyaluronan networking via Ugi’s condensation using lysine as cross-linker diamine. Carbohydr Polym 53(3):311–316CrossRef
69.
Zurück zum Zitat Bu H, Kjøniksen A-L, Knudsen KD, Nyström B (2004) Rheological and structural properties of aqueous alginate during gelation via the Ugi multicomponent condensation reaction. Biomacromolecules 5(4):1470–1479CrossRef Bu H, Kjøniksen A-L, Knudsen KD, Nyström B (2004) Rheological and structural properties of aqueous alginate during gelation via the Ugi multicomponent condensation reaction. Biomacromolecules 5(4):1470–1479CrossRef
70.
Zurück zum Zitat Bu H, Kjøniksen A-L, Nyström B (2005) Effects of pH on dynamics and rheology during association and gelation via the Ugi reaction of aqueous alginate. Eur Polym J 41(8):1708–1717CrossRef Bu H, Kjøniksen A-L, Nyström B (2005) Effects of pH on dynamics and rheology during association and gelation via the Ugi reaction of aqueous alginate. Eur Polym J 41(8):1708–1717CrossRef
71.
Zurück zum Zitat Sehlinger A, Dannecker P-K, Kreye O, Meier MAR (2014) Diversely substituted polyamides: macromolecular design using the Ugi four-component reaction. Macromolecules 47(9):2774–2783CrossRef Sehlinger A, Dannecker P-K, Kreye O, Meier MAR (2014) Diversely substituted polyamides: macromolecular design using the Ugi four-component reaction. Macromolecules 47(9):2774–2783CrossRef
72.
Zurück zum Zitat Sehlinger A, Schneider R, Meier MAR (2014) Ugi reactions with CO2: access to functionalized polyurethanes, polycarbonates, polyamides or polyhydantoins. Macromol Rapid Commun 35(21):1866–1871 Sehlinger A, Schneider R, Meier MAR (2014) Ugi reactions with CO2: access to functionalized polyurethanes, polycarbonates, polyamides or polyhydantoins. Macromol Rapid Commun 35(21):1866–1871
73.
Zurück zum Zitat Yang B, Zhao Y, Fu C, Zhu C, Zhang Y, Wang S, Wei Y, Tao L (2014) Introducing the Ugi reaction into polymer chemistry as a green click reaction to prepare middle-functional block copolymers. Polym Chem 5(8):2704–2708CrossRef Yang B, Zhao Y, Fu C, Zhu C, Zhang Y, Wang S, Wei Y, Tao L (2014) Introducing the Ugi reaction into polymer chemistry as a green click reaction to prepare middle-functional block copolymers. Polym Chem 5(8):2704–2708CrossRef
74.
Zurück zum Zitat Tao L, Xu J, Gell D, Davis TP (2010) Synthesis, characterization, and bioactivity of mid-functional polyHPMA−lysozyme bioconjugates. Macromolecules 43(8):3721–3727CrossRef Tao L, Xu J, Gell D, Davis TP (2010) Synthesis, characterization, and bioactivity of mid-functional polyHPMA−lysozyme bioconjugates. Macromolecules 43(8):3721–3727CrossRef
75.
Zurück zum Zitat Barner-Kowollik C, Du Prez FE, Espeel P, Hawker CJ, Junkers T, Schlaad H, Van Camp W (2011) “Clicking” polymers or just efficient linking: what is the difference? Angew Chem Int Ed 50(1):60–62CrossRef Barner-Kowollik C, Du Prez FE, Espeel P, Hawker CJ, Junkers T, Schlaad H, Van Camp W (2011) “Clicking” polymers or just efficient linking: what is the difference? Angew Chem Int Ed 50(1):60–62CrossRef
76.
Zurück zum Zitat Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40(11):2004–2021CrossRef Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40(11):2004–2021CrossRef
77.
Zurück zum Zitat Jevševar S, Kunstelj M, Porekar VG (2010) PEGylation of therapeutic proteins. Biotechnol J 5(1):113–128CrossRef Jevševar S, Kunstelj M, Porekar VG (2010) PEGylation of therapeutic proteins. Biotechnol J 5(1):113–128CrossRef
78.
Zurück zum Zitat Yang B, Zhao Y, Wang S, Zhang Y, Fu C, Wei Y, Tao L (2014) Synthesis of multifunctional polymers through the Ugi reaction for protein conjugation. Macromolecules 47(16):5607–5612CrossRef Yang B, Zhao Y, Wang S, Zhang Y, Fu C, Wei Y, Tao L (2014) Synthesis of multifunctional polymers through the Ugi reaction for protein conjugation. Macromolecules 47(16):5607–5612CrossRef
79.
Zurück zum Zitat Yang B, Zhao Y, Ren X, Zhang X, Fu C, Zhang Y, Wei Y, Tao L (2015) The power of one-pot: a hexa-component system containing π–π stacking, Ugi reaction and RAFT polymerization for simple polymer conjugation on carbon nanotubes. Polym Chem 6:509–513 Yang B, Zhao Y, Ren X, Zhang X, Fu C, Zhang Y, Wei Y, Tao L (2015) The power of one-pot: a hexa-component system containing π–π stacking, Ugi reaction and RAFT polymerization for simple polymer conjugation on carbon nanotubes. Polym Chem 6:509–513
80.
Zurück zum Zitat Barreto AdFS, Vercillo OE, Birkett MA, Caulfield JC, Wessjohann LA, Andrade CKZ (2011) Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions. Org Biomol Chem 9(14):5024–5027CrossRef Barreto AdFS, Vercillo OE, Birkett MA, Caulfield JC, Wessjohann LA, Andrade CKZ (2011) Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions. Org Biomol Chem 9(14):5024–5027CrossRef
81.
Zurück zum Zitat Wessjohann LA, Tran TPT, Westermann B (2008) Method for producing condensation products from n-substituted glycine derivatives (peptoids) by sequential Ugi-multicomponent reactions. Patent WO 2008/022800 Wessjohann LA, Tran TPT, Westermann B (2008) Method for producing condensation products from n-substituted glycine derivatives (peptoids) by sequential Ugi-multicomponent reactions. Patent WO 2008/022800
82.
Zurück zum Zitat Barreto AdFS, Vercillo OE, Wessjohann LA, Andrade CKZ (2014) Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids. Beilstein J Org Chem 10:1017–1022CrossRef Barreto AdFS, Vercillo OE, Wessjohann LA, Andrade CKZ (2014) Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids. Beilstein J Org Chem 10:1017–1022CrossRef
Metadaten
Titel
Passerini and Ugi Multicomponent Reactions in Polymer Science
verfasst von
Ansgar Sehlinger
Michael A. R. Meier
Copyright-Jahr
2015
DOI
https://doi.org/10.1007/12_2014_298

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