Exploiting the divalent nature of isonitriles: a novel Pictet-Spengler amidination process

TETRAHEDRON LETTERS

卷:55

Article

Medda, Federico^1,2  Hulme, Christopher^1,2,3 

[1] Univ Arizona, Coll Pharm, Tucson, AZ 85721 USA

[2] BIO5 Oro Valley, Oro Valley, AZ 85737 USA

[3] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

关键词: Isonitrile;    Multicomponent reaction;    Amidine;    Pictet-Spengler;   

DOI  :  10.1016/j.tetlet.2014.04.043

来源: Elsevier

【 摘 要 】

An isocyanide-based multicomponent reaction (IMCR) utilized for the rapid assembly of novel, biologically relevant dihydropyrrolo[1,2-a]quinoxalines-amidines is herein presented. Starting from 1-(2-aminophenyl)pyrroles, aldehydes, and isonitriles, the target heterocyclic scaffold is assembled in a one-pot, operationally friendly process. With three points of diversity and formation of three chemical bonds in one step, this strategy proves to be very general. Novel, mild methodology for the generation of amidines from secondary amine anilines and isonitriles is also introduced. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

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