Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition

Michael De Rosa, David Arnold, Miroslav Medved'

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.

Original languageEnglish (US)
Pages (from-to)3991-3994
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number23
DOIs
StatePublished - Jun 4 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition'. Together they form a unique fingerprint.

Cite this