Facile synthesis of 1-substituted 2-amino-3-cyanopyrroles: New synthetic precursors for 5,6-unsubstituted pyrrolo[2,3-d]pyrimidines

Tun Cheng Chien, Eric A. Meade, Jack M. Hinkley, Leroy B. Townsend

研究成果: 雜誌貢獻文章同行評審

48 引文 斯高帕斯(Scopus)

摘要

(Equation Presented) 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3- cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).

原文英語
頁(從 - 到)2857-2859
頁數3
期刊Organic Letters
6
發行號17
DOIs
出版狀態已發佈 - 2004 八月 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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