nach oben

Clean Technologies and Environmental Policy

Erschienen in:

13.11.2019 | Original Paper

Ultrasound-assisted fabrication of N-cyano-N-arylbenzenesulfonamides at ambient temperature: improvements with biosynthesized Ag/feldspar nanocomposite

verfasst von: Mahmoud Nasrollahzadeh, Fatemeh Ghorbannezhad, Rajender S. Varma

Erschienen in: Clean Technologies and Environmental Policy | Ausgabe 1/2020

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

A mild and effective method for ultrasound-assisted N-sulfonylation of arylcyanamides with aryl sulfonyl chloride is introduced at ambient temperature; synthesis of assorted derivatives of N-cyano-N-arylbenzenesulfonamide as electrophilic cyanation agent can be further improved using Ag/feldspar nanocomposite, accessible via an simple, eco-friendly and inexpensive method using Hedera helix leaf extract. The important advantages of this method include clean conditions, high purity and yield, and easy workup procedure with minimum generation of waste. The structure and morphology nanocatalyst were characterized by energy-dispersive X-ray spectroscopy, field emission scanning electron microscope, transmission electron microscopy, X-ray powder diffraction and elemental mapping.

Graphic abstract

Vorheriger Artikel Effect of the climatic conditions in energy efficiency of Spanish existing dwellings

Nächster Artikel Inventory and life cycle assessment of an Italian automotive painting process

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Anderson RS, Anderson SP (2010) Geomorphology: the mechanics and chemistry of landscapes. Cambridge University Press, Cambridge, p 187

Bankar A, Joshi B, Kumar AR, Zinjarde S (2010) Banana peel extract mediated novel route for the synthesis of silver nanoparticles. Colloids Surf A 368:58–63

Bhat SV, Robinson D, Moses JE, Sharma P (2016) Synthesis of oxadiazol-5-imines via the cyclizative capture of in Situ generated cyanamide ions and nitrile oxides. Org Lett 18(5):1100–1103

Buono FG, Chidambaram R, Mueller RH, Waltermire RE (2008) Insights into palladium-catalyzed cyanation of bromobenzene: additive effects on the rate-limiting step. Org Lett 10:5325–5328

Chatel G (2017) Sonochemistry-new opportunities for green chemistry. World Scientific, London, p 170

Chen J, Sun Y, Liu B, Liu D, Cheng J (2012) The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfonates. Chem Commun 48:449–451

Cravotto G, Cintas P (2007) Forcing and controlling chemical reactions with ultrasound. Angew Chem Int Ed 46:5476–5478

Cristau HJ, Ouali A, Spindler JF, Taillefer M (2005) Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides. Chem Eur J 11:2483–2492

Fleming F, Yao L, Ravikumar PC, Funk L, Shook BC (2010) Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore. J Med Chem 53:7902–7917

Gomtsyan A (2012) Heterocycles in drugs and drug discovery. Chem Heterocycl Compd 48:7–10

Gong T-J, Xiao B, Cheng W-M, Su W, Xu J, Liu Z-J, Liu L, Fu Y (2013) Rhodium-catalyzed directed C–H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide. J Am Chem Soc 135:10630–10633

Gu L-J, Jin C, Wang R, Ding H-Y (2014) Rhodium catalyzed ortho-cyanation of arylphosphates with N-cyano-N-phenyl-p-toluenesulfonamide. ChemCatChem 6:1225–1228

Habibi D, Nasrollahzadeh M, Bayat Y (2011) AlCl₃ as an effective lewis acid for the synthesis of arylaminotetrazoles. Synth Commun 41:2135–2145

Heydari S, Habibi D (2018) The Bismarck Brown Y based functional polymer-bound palladium nanoparticles as a capable catalyst for the synthesis of N-arylsulfonyl cyanamides. Polyhedron 154:138–147

Jordan AM, Roughley SD (2009) Drug discovery chemistry: a primer for the non-specialist. Drug Discov Today 14:731–744

Khodadadi B, Bordbar M, Nasrollahzadeh M (2017) Green synthesis of Pd nanoparticles at Apricot kernel shell substrate using Salvia hydrangea extract: catalytic activity for reduction of organic dyes. J Colloid Interface Sci 490:1–10

Kiyokawa K, Nagata T, Minakata S (2016) Electrophilic cyanation of boron enolates: efficient access to various β-ketonitrile derivatives. Angew Chem Int Ed 55:10458–10462

Kleemann A, Engel J, Kutscher B, Reichert D (2002) Pharmaceutical substances: syntheses, patents applications. Org Proc Res Dev 6(5):739–740

Kumar KM, Mandal BK, Tammina SK (2013) Green synthesis of nano platinum using naturally occurring polyphenols. RSC Adv 3:4033–4039

Kuna E, Behling R, Valange S, Chatel G, Colmenares JC (2017) Sonocatalysis: a potential sustainable pathway for the valorization of lignocellulosic biomass and derivatives. Top Curr Chem 375:41–61

Kurzer F (1949a) Cyanamides. Part I. The synthesis of substituted arylsulphonylcyanamides. J Chem Soc 1034–1038

Kurzer F (1949b) Cyanamides. Part III. The formation of substituted triazines from o-halogenophenylureas and arylsulphonyl chlorides. J Chem Soc 3029–3033

Larock RC (1989) Comprehensive organic transformations, a guide to functional group preparations, In comprehensive organic transformations. VCH, New York, p 819

Lee KS, El-Sayed MA (2006) Gold and silver nanoparticles in sensing and imaging: sensitivity of plasmon response to size, shape, and metal composition. J Phys Chem B 110:19220–19225

Li JJ (2013) Heterocyclic chemistry in drug discovery. Wiley, Hoboken, pp 1–647

Lin C-C, Hsieh T-H, Liao P-Y, Liao Z-Y, Chang C-W, Shih Y-C, Yeh W-H, Chien T-C (2014) Practical synthesis of N-substituted cyanamides via Tiemann rearrangement of amidoximes. Org Lett 16:892–895

Metcalfe DJ (2005) Hedera helix L. J Ecol 93:632–648

Mishra A, Vats TK, Deb I (2016) Ruthenium-catalyzed direct and selective C-H cyanation of N-(hetero)aryl-7-azaindoles. J Org Chem 81:6525–6534

Momeni S, Nasrollahzadeh M, Rustaiyan A (2016) Green synthesis of the Cu/ZnO nanoparticles mediated by Euphorbia prolifera leaf extract and investigation of their catalytic activity. J Colloid Interface Sci 472:173–179

Nair LS, Laurencin CT (2007) Silver nanoparticles: synthesis and therapeutic applications. J Biomed Nanotechnol 3:301–316

Nasrollahzadeh M, Mahmoudi-Gom-Yek S, Motahharifar N, Ghafori Gorab M (2019) Recent developments in the plant-mediated green synthesis of Ag-based nanoparticles for environmental and catalytic applications. Chem Rec. https://doi.org/10.1002/tcr.201800202 CrossRef

Nekrasov DD (2004) Synthesis and chemical transformations of mono- and disubstituted cyanamides. Russ J Org Chem 40:1387–1402

Rappoport Z (1970) In chemistry of the cyano group. Wiley, London, p 121

Rudnick RL, Gao S (2003) Composition of the continental crust. In: Holland HD, Turekian KK (eds) Treatise on geochemistry. Treatise on geochemistry, vol 3. Elsevier Science, New York, pp 1–64

Sajjadi M, Nasrollahzadeh M, Sajadi SM (2017) Green synthesis of Ag/Fe₃O₄ nanocomposite using Euphorbia peplus Linn leaf extract and evaluation of its catalytic activity. J Colloid Interface Sci 497:1–13

Schareina T, Zapf A, Cotte A, Gotta M, Beller M (2011) A versatile protocol for copper-atalyzed cyanation of aryl and heteroaryl bromides with acetone cyanohydrin. Adv Synth Catal 353:777–780

Su W, Gong TJ, Xiao B, Fu Y (2015) Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent. Chem Commun 51:11848–11851

Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M (2003) A convenient and efficient procedure for the palladium-catalyzed cyanation of aryl halides using trimethylsilylcyanide. J Organomet Chem 684:50–55

Ushkov AV, Grushin VV (2011) Rational catalysis design on the basis of mechanistic understanding: highly efficient Pd-catalyzed cyanation of aryl bromides with NaCN in recyclable solvents. J Am Chem Soc 133:10999–11005

Varma RS, Naicker KP (1998) Ultrasound accelerated permanganate oxidation: an improved procedure for the synthesis of 1,2-cis diols from olefins. Tetrahedron Lett 39:7463–7466

Walsh CT (2015) Nature loves nitrogen heterocycles. Tetrahedron Lett 56:3075–3081

Wang R, Falck JR (2013) Rhodium(I)-catalyzed N-CN bond cleavage: intramolecular β-cyanation of styrenes. Chem Commun 49:6516–6518

Xu H, Zeiger BW, Suslick K (2013) Sonochemical synthesis of nanomaterials. Chem Soc Rev 42:2555–2567

Yeung PY, So CM, Lau CP, Kwong FY (2011) A mild and efficient palladium-catalyzed cyanation of aryl chlorides with K₄[Fe(CN)₆]. Org Lett 13:648–651

Titel: Ultrasound-assisted fabrication of N-cyano-N-arylbenzenesulfonamides at ambient temperature: improvements with biosynthesized Ag/feldspar nanocomposite
verfasst von: Mahmoud Nasrollahzadeh
Fatemeh Ghorbannezhad
Rajender S. Varma
Publikationsdatum: 13.11.2019
Verlag: Springer Berlin Heidelberg
Erschienen in: Clean Technologies and Environmental Policy / Ausgabe 1/2020
Print ISSN: 1618-954X
Elektronische ISSN: 1618-9558
DOI: https://doi.org/10.1007/s10098-019-01779-w

Springer Professional

Abstract

Graphic abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 1/2020

Modeling and performance analysis of subcritical and supercritical coal-fired power plants with biomass co-firing and CO2 capture

Mapping incinerability of municipal solid waste in Indian sub-continent

A fuzzy analytic hierarchy process for the site selection of the Philippine algal industry

Effect of manufacturing and installation location on environmental impact payback time of solar power

A cleaner enzymatic approach for producing non-phthalate plasticiser to replace toxic-based phthalates

Biochar mines: Panacea to climate change and energy crisis?