Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage

Shun Ichi Yamamoto, Kana Okamoto, Makiko Murakoso, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re 2(CO) 10, gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.

Original languageEnglish
Pages (from-to)3182-3185
Number of pages4
JournalOrganic Letters
Volume14
Issue number12
DOIs
Publication statusPublished - Jun 15 2012
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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