Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine Journal Article


Authors: Perl, N. R.; Ide, N. D.; Prajapati, S.; Perfect, H. H.; Durón, S. G.; Gin, D. Y.
Article Title: Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine
Abstract: (Chemical Presented) A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles. Copyright © 2010 American Chemical Society.
Keywords: unclassified drug; pyrimidines; alkylation; amination; pyrimidine derivative; vinyl derivative; synthesis; synthesis (chemical); stereoisomerism; spiro compounds; convergent synthesis; chemical bond; nucleophile; acetylene; alkynes; nucleophiles; 2-aminopyrimidine; 2-aminopyrimidines; carbodiimides; crambidine; hydroaminations; isomers; alkyne derivative; cyanamide; annulation reaction; guanidine; imidoesters
Journal Title: Journal of the American Chemical Society
Volume: 132
Issue: 6
ISSN: 0002-7863
Publisher: American Chemical Society  
Date Published: 2010-01-01
Start Page: 1802
End Page: 1803
Language: English
DOI: 10.1021/ja910831k
PUBMED: 20095555
PROVIDER: scopus
PMCID: PMC2839241
DOI/URL:
Notes: --- - "Cited By (since 1996): 5" - "Export Date: 20 April 2011" - "CODEN: JACSA" - "Source: Scopus"
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  1. Nicholas R Perl
    3 Perl
  2. David Y Gin
    41 Gin