2-氨基吡啶,2-氨基嘧啶,2-氨基吡嗪或2-氨基噻吩等含有H2N-C=N结构化合物,醛和异腈一锅法缩合得到氨基咪唑的反应。此反应是多组分反应,机理与Ugi反应类似。
反应机理
醛和氨先形成亚胺,亚胺再与异腈关环得到产物。
反应实例
N-t-Butyl-8-(4-chlorophenyl)-3H-imidazo[1,2-i]purin-7-amine (5). t-Butyl isocyanide 3 (0.17 g,2 mmol) and ZrCl4 (47 mg, 10 mol%) were added to stirred adenine 1 (0.27 g, 2 mmol) and 4-chlorobenzaldehyde 2 (0.28 g, 2 mmol) in 5 mL DMSO and the mixture was heated at 70 ℃ for 7.5 h. Most of DMSO was evaporated at 50–60 ℃(2 mm) and the residue was chromatographed on silica (EA–hexane) to afford 5 (0.462 g, 68%), mp 229–231 ℃.
【Guchhait SK, Tet Lett, 2011, 52, 56】
相关文献
1 Groebke K Synlett 1998 661
2 Blackburn C Tet lett 1998 39 3635
3 Bienayme H Angew Chem Int 1998 37 2234
4 Guchhait SK Synlett 2009 628
5R Ivachtchenko AV Russ Chem Rev 2010 79 787
6 Guchhait SK Tet Lett 2011 52 56
编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 192-193.
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