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2014 | OriginalPaper | Buchkapitel

The S _N ^H -Amination of Heteroaromatic Compounds

verfasst von : Anna V. Gulevskaya, Alexander F. Pozharskii

Erschienen in: Metal Free C-H Functionalization of Aromatics

Verlag: Springer International Publishing

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Abstract

The review surveys the data on amination of electron-deficient aromatic heterocycles by using the methodology of nucleophilic substitution of hydrogen (S _N ^H ). The recent advances in this area involve many new aspects of the S _N ^H -amination, including a wide range of heteroaromatic substrates and new types of aminating reagents, metal-free catalysts, solvents, and the hydride ion acceptors. The review demonstrates that the S _N ^H approach is becoming an increasingly popular and important synthetic alternative to the classical and transition metal-catalyzed amino-dehalogenation reactions.

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Vorheriges Kapitel C–H Functionalization of Heteroaromatic N-Oxides

Nächstes Kapitel Electrochemical C–H Functionalization of Arenes and Heteroarenes

Corey EJ, Czakó B, Kürti L (2007) Molecules and medicine. Wiley, Hoboken

Pozharskii AF, Soldatenkov AT, Katritzky AR (2011) Heterocycles in life and society. Wiley, Chichester

Travis AS (2007) In: Rappoport Z (ed) The chemistry of anilines. Wiley, Chichester, Chap 13, p 715

Terrier F (1991) Aromatic nucleophilic substitution reaction. Wiley-VCH, New York

Kienle M, Dubbaka SR, Brade K, Knochel P (2007) Eur J Org Chem 25:4166

Hartwig JF (2008) Nature 455:314

Chichibabin AE, Zeide OA (1914) Zh Russ Phys Khim Obsh 46:1216

Chupakhin ON, Postovsky IYa (1976) Russ Chem Rev 45:454

Pozharskii AF, Simonov AM (1971) Chichibabin Amination of Heterocycles. University Press, Rostov-on-Don (in Russian)

10.

Pozharskii AF, Simonov AM, Doron’kin VN (1978) Russ Chem Rev 47:1042

11.

van der Plas HC (1978) Acc Chem Res 11:462

12.

van der Plas HC, Woźniak M (1986) Croat Chem Acta 59:33

13.

van der Plas HC (1987) Khim Geterotsikl Soedin 1011

14.

Mąkosza M, Winiarski J (1987) Acc Chem Res 20:282

15.

McGill CK, Rappa A (1988) Adv Heterocycl Chem 44:1

16.

Chupakhin ON, Charushin VN, van der Plas H (1988) Tetrahedron 44:1

17.

Mąkosza M (1989) Russ Chem Rev 58:747

18.

Mąkosza M (1991) Synthesis 103

19.

Woźniak M, van der Plas H (1993) Acta Chem Scand 47:95

20.

Mąkosza M (1996) Russ Chem Bull 45:491

21.

Mąkosza M, Wojciechowski K (1997) Liebigs Ann Chem 1805

22.

Mąkosza M, Kwast A (1998) J Phys Org Chem 11:341

23.

Mąkosza M, Staliński (1999) Polish J Chem 73:151

24.

van der Plas HC (1999) Adv Heterocycl Chem 74:9

25.

Mąkosza M, Wojciechowski K (2001) Heterocycles 54:445

26.

Chupakhin ON, Beresnev DG (2002) Russ Chem Rev 71:707

27.

van der Plas HC (2002) Targets Heterocyclic Syst 5:1

28.

Chupakhin ON, Charushin VN, Rusinov VL (2003) In: Rakhmankulov DL (ed) Panorama of modern chemistry in Russia: modern organic synthesis. Chemistry, Moscow, p. 99 (in Russian)

29.

Mąkosza M, Wojciechowski K (2004) Chem Rev 104:2631

30.

van der Plas H (2004) Adv Heterocycl Chem 86:1

31.

Charushin VN, Chupakhin ON (2004) Pure Appl Chem 76:1621

32.

Mąkosza M, Paszewski M (2005) Polish J Chem 79:163

33.

Charushin VN, Chupakhin ON (2007) Mendeleev Commun 17:249

34.

Gulevskaya AV, Pozharskii AF (2007) Adv Heterocycl Chem 93:57

35.

Gulevskaya AV, Pozharskii AF (2008) Russ Chem Bull 57:913

36.

Mąkosza M (2010) Chem Soc Rev 39:2855

37.

Mąkosza M (2011) Synthesis 2341

38.

Gulevskaya AV, Tyaglivaya IN (2012) Russ Chem Bull 61:1321

39.

Chupakhin ON, Charushin VN, van der Plas H (1994) Nucleophilic aromatic substitution of hydrogen. Academic, New York

40.

Novikov VN, Pozharskii AF, Doronkin VN (1976) Chem Heterocycl Compd 12:210

41.

Rudnitskaya A, Török B, Dransfield T (2011) Comput Theor Chem 963:191

42.

Banerjee S, Voit B, Heinrich G, Böhme F (2012) Tetrahedron Lett 53:2236

43.

Varlamov AV, Levov AN, Toze F, Chernyshev AI, Davydov VV, Ryabov MA, Egorova OA (2002) Chem Heterocycl Compd 38:1484

44.

Bergstrøm FW (1934) J Amer Chem Soc 56:1748

45.

Bergstrøm FW (1937) J Org Chem 2:411

46.

Zoltewich JA, Helmick LS (1972) J Amer Chem Soc 94:682

47.

Hara H, van der Plas H (1982) J Heterocycl Chem 19:1285

48.

Bergstrøm FW, Sturz HG, Tracy HW (1946) J Org Chem 11:239

49.

Counotte-Potman A, van der Plas HC (1981) J Heterocycl Chem 18:123

50.

Woźniak M, Barański A, Szpakiewicz B (1991) Liebigs Ann Chem 875

51.

Zoltewicz JA, Helmick LS, Oestreich TM, King RW, Kandetzki PE (1973) J Org Chem 38:1947

52.

Tondys H, van der Plas H, Woźniak M (1985) J Heterocycl Chem 22:353

53.

Woźniak M, Barański A, Nowak K (1987) J Org Chem 52:5643

54.

Cheng J, Liu ZL, Yao QZ, Zhou XL, Wang AL (2009) Chin J Explosive Propellants 32:5

55.

Demidov OP, Borovlev IV, Saigakova NA, Nemykina OA, Demidova NV, Pisarenko SV (2011) Chem Heterocycl Compd 47:114

56.

Grzegożek M, Szpakiewicz B (2006) J Heterocycl Chem 43:425

57.

Szpakiewicz B, Grzegożek M (2004) Russ J Org Chem 40:829

58.

Woźniak M, Grzegożek M, Roszkiewicz W, Szpakiewicz B (1995) Recl Trav Chim Pays Bas 114:13

59.

Bakke JM, Svensen H (2001) Tetrahedron Lett 42:4393

60.

Kozhevnikov DN, Rusinov VL, Chupakhin ON (2002) Adv Heterocycl Chem 82:261

61.

Surange SS, Rajappa S (1998) Tetrahedron Lett 39:7169

62.

Bianchi L, Maccagno M, Petrillo G, Sancassan F, Tavani C, Morganti S, Rizzato E, Spinelli D (2007) J Org Chem 72:5771

63.

Borovlev I, Demidov O, Saigakova N, Pisarenko S, Nemykina O (2011) J Heterocycl Chem 48:1206

64.

Crosby AH, Lutz RE (1956) J Am Chem Soc 78:1233

65.

Tsizin YS (1978) Chem Heterocycl Compd 14:925

66.

Kutyrev AA, Moskva VV (1991) Russ Chem Rev 60:72

67.

Choi HY, Chi DY (2004) Tetrahedron 60:4945

68.

Valderrama JA, Ibacache JA, Arancibia V, Rodriguez J, Theoduloz C (2009) Bioorg Med Chem 17:2894

69.

Valderrama JA, Ibacache JA (2009) Tetrahedron Lett 50:4361

70.

Loskutov VA (2011) Russ J Org Chem 47:1551

71.

Xiao Y, Liu F, Qian X, Cui J (2005) Chem Commun 239

72.

Liu F, Xiao Y, Qian X, Zhang Z, Cui J, Cui D, Zhang R (2005) Tetrahedron 61:11264

73.

Firouzabadi H, Vessal B (1982) Naderi M 23:1847

74.

Pozharskii AF, Gulevskaya AV, Kuz’menko VV (1988) Chem Heterocycl Compd 24:1404

75.

Gulevskaya AV, Maes BUW, Meyers C (2007) Synlett 71

76.

Goryunenko VV, Gulevskaya AV, Pozharskii AF (2004) Russ Chem Bull 53:846

77.

Gulevskaya AV, Burov ON, Pozharskii AF, Kletskii ME, Korbukova IN (2008) Tetrahedron 64:696

78.

Burov ON, Gulevskaya AV, Pozharskii AF (2009) Chem Heterocycl Compd 45:475

79.

Besedin DV, Gulevskaya AV, Pozharskii AF (2000) Mendeleev Commun 10:150

80.

Goryunenko VV, Gulevskaya AV, Pozharskii AF (2003) Russ Chem Bull 52:441

81.

Gulevskaya AV, Dang VS, Pozharskii AF (2003) Russ Chem Bull 52:1403

82.

Gulevskaya AV, Besedin DV, Pozharskii AF, Starikova ZA (2001) Tetrahedron Lett 42:5981

83.

Besedin DV, Gulevskaya AV, Pozharskii AF (2000) Chem Heterocycl Compd 36:1213

84.

Gulevskaya AV, Pozharskii AF, Besedin DV, Serduke OV, Starikova ZA (2002) Mendeleev Commun 157

85.

Gulevskaya AV, Serduke OV, Pozharskii AF, Besedin DV (2003) Tetrahedron 59:7669

86.

Serduke OV, Gulevskaya AV, Pozharskii AF, Starikova ZA, Profatilova IA (2006) Tetrahedron 62:652

87.

Gulevskaya AV, Maes BUW, Meyers C, Herrebout H, van der Veken BJ (2006) Eur J Org Chem 5305

88.

Verbeeck S, Herrebout WA, Gulevskaya AV, van der Veken BJ, Maes BUW (2010) J Org Chem 75:5126

89.

Budyka MF, Terent’ev PB, Kost AN (1978) Chem Heterocycl Compd 14:663

90.

Garnier E, Audoux J, Pasquinet E, Suzenet F, Poullain D, Lebret B, Guillaumet G (2004) J Org Chem 69:7809

91.

Patriciu OI, Pillard C, Fînaru ALT, Săndulescu I, Guillaumet G (2007) Synthesis 3868

92.

Gulevskaya AV, Tyaglivaya IN, Verbeeck S, Maes BUW, Tkachuk AV (2011) ARKIVOC (ii):238

93.

Valderrama JA, Ibacache JA, Rodriguez J, Theoduloz C, Benites J (2011) Eur J Med Chem 46:3398

94.

Cho SH, Kim JY, Lee SY, Chang S (2009) Angew Chem Int Ed 48:9127

95.

Kim JY, Cho SH, Joseph J, Chang S (2010) Angew Chem Int Ed 49:9899

96.

Li Y, Xie Y, Zhang R, Jin K, Wang X, Duan C (2011) J Org Chem 76:5444

97.

Wang J, Hou JT, Wen J, Zhang J, Yu XQ (2011) Chem Commun 47:3652

98.

Joseph J, Kim JY, Chang S (2011) Chem Eur J 17:8294

99.

Wertz S, Kodama S, Studer A (2011) Angew Chem Int Ed 50:11511

100.

Froehr T, Sindlinger CP, Kloeckner U, Finkbeiner P, Nachtsheim BJ (2011) Org Lett 13:3754

101.

Kloeckner U, Weckenmann NM, Nachtsheim BJ (2012) Synlett 23:97

102.

Lamani M, Prabhu KR (2011) J Org Chem 76:7938

103.

Wagh YS, Sawant DN, Bhanage BM (2012) Tetrahedron Lett 53:3482

104.

Suwiński J, Świerczek K (2001) Tetrahedron 57:1639

105.

Buluchevskaya NA, Gulevskaya AV, Pozharskii AF (2003) Chem Heterocycl Compd 39:87

106.

Kozhevnikov VN, Prokhorov AM, Kozhevnikov DN, Rusinov VL, Chupakhin ON (2000) Russ Chem Bull 49:1122

107.

Prokhorov AM, Kozhevnikov DN, Rusinov VL, Chupakhin ON (2003) Russ Chem Bull 52:1195

108.

Storz T, Marti R, Meier R, Nury P, Roeder P, Zhang K (2004) Org Process Res Dev 8:663

109.

Gerster JF, Lindstrom KJ, Miller RL, Tomai MA, Birmachu W, Bomersine SN, Gibson SJ, Imbertson LM, Jacobson JR, Knafla RT, Maye PV, Nikolaides N, Oneyemi FY, Parkhurst GJ, Pecore SE, Reiter MJ, Scribner LS, Testerman TL, Thompson NJ, Wagner TL, Weeks CE, Andre JD, Lagain D, Bastard Y, Lupu M (2005) J Med Chem 48:3481

110.

Couturier M, Le T (2006) Org Process Res Dev 10:534

111.

Solekhova MA, Kurbatov YV (2002) Russ J Org Chem 38:1192

112.

Londregan AT, Jennings S, Wei L (2010) Org Lett 12:5254

113.

Londregan AT, Jennings S, Wei L (2011) Org Lett 13:1840

114.

Yin J, Xiang B, Huffman MA, Raab CE, Davies IW (2007) J Org Chem 72:4554

115.

Farrell RP, Elipe MVS, Bartberger MD, Tedrow JS, Vounatsos F (2013) Org Lett 15:168

116.

Abramovich RA, Singer GM (1969) J Am Chem Soc 91:5672

117.

Maley PJ, Bilodeau MT (2002) Org Lett 4:3127

118.

Couturier M, Caron L, Tumidajski S, Jones K, White TD (2006) Org Lett 8:1929

119.

Keith JM (2010) J Org Chem 75:2722

120.

Keith JM (2008) J Org Chem 73:327

121.

Kiselyov AS (2005) Chem Soc Rev 34:1031

122.

Dalinger IL, Cherkasova TI, Popova GP, Shkineva TK, Vatsadze IA, Shevelev SA, Kanishchev MI (2009) Russ Chem Bull 58:410

123.

Asahara M, Nagamatsu M, Tohda Y, Nishiwaki N, Ariga M (2005) Arkivoc (i):1

124.

Nishiwaki N (2010) Molecules 15:5174

125.

Enguehard C, Allouchi H, Gueiffier A, Buchwald SL (2003) J Org Chem 68:5614

126.

Woźniak M, van der Plas HC (1978) J Heterocycl Chem 15:731

127.

Tišler M (2011) Acta Chim Slov 58:9

128.

van der Plas HC (2000) J Heterocycl Chem 37:427

129.

Saldago A, Varela C, Collazo AMG, García F, Pevarello P, Alkorta I, Elguero J (2011) J Mol Struc 987:13

130.

Gondela A, Gabański R, Walczak K (2004) Tetrahedron Lett 45:8007

131.

El Ashry ESH, Nadeem S, Shah MR, El Kilany Y (2010) Adv Heterocycl Chem 101:161

132.

Donskaya OV, Dolgushin GV, Lopyrev VA (2002) Chem Heterocycl Compd 38:371

133.

Schmidt RD, Lee GS, Pagoria PF, Mitchell AR (2001) J Heterocycl Chem 38:1227

134.

Suwiński J, Świerczek K, Glowiak T (1993) Tetrahedron 49:5339

135.

Suwiński J, Świerczek K (1996) Chem Heterocycl Compd 32:1040

136.

Mąkosza M, Białecki M (1998) J Org Chem 63:4878

137.

Seko S, Miyake K (1998) Chem Commun 1519

138.

Bakke JM, Svensen H, Trevisan R (2001) J Chem Soc Perkin Trans 1:376

139.

Hollins RA, Merwin LH, Nissan RA, Wilson WS, Gilardi R (1996) J Heterocycl Chem 33:895

140.

Grzegożek M (2008) J Heterocycl Chem 45:1879

141.

Grzegożek M, Szpakiewicz B, Kowalski P (2009) Arkivoc (vi):84

142.

Nasielski-Hinkens R, Kotel J, Lecloux T, Nasielski J (1989) Synth Commun 19:511

143.

Katritzky AR, Laurenzo KS (1988) J Org Chem 53:3978

144.

Donskaya OV, Elokhina VN, Nakhmanovich AS, Vakil’skaya TI, Larina LI, Vokin AI, Albanov AI, Lopyrev VA (2002) Tetrahedron Lett 43:6613

145.

Titova IA, Vakul’skaya TI, Larina LI, Mizandrontsev MI, Volkov VA, Dolgushin GV, Lopyrev VA (2005) Russ J Org Chem 41:1306

146.

Lopyrev VA, Elokhina VN, Krylova OV, Nakhmanovich AS, Larina LI, Sorokin MS, Vokin AI (1999) Chem Heterocycl Compd 35:1109

147.

Elokhina VN, Krylova OV, Larina LI, Nakhmanovich AS, Sorokin MS, Volkova KA, Lopyrev VA (2000) Chem Heterocycl Compd 36:476

148.

Vakul’skaya TI, Titova IA, Larina LI, Verkhozina ON, Dolgushin GV, Lopyrev VA (2006) Chem Heterocycl Compd 42:1427

149.

Ostrowski S, Grzyb S (2012) Tetrahedron Lett 53:6355

Titel: The S N H -Amination of Heteroaromatic Compounds
verfasst von: Anna V. Gulevskaya
Alexander F. Pozharskii
Verlag: Springer International Publishing
Buch: Metal Free C-H Functionalization of Aromatics
Print ISBN: 978-3-319-07018-6

Electronic ISBN: 978-3-319-07019-3

Copyright-Jahr: 2014
DOI: https://doi.org/10.1007/7081_2013_114

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