Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach

Sujin Park, Ikyon Kim

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A new synthetic approach to 6,7-disubstituted indolizines has been developed from pyrrole-2-carboxaldehydes and allyl bromides via two successive base-mediated reactions. As three-carbon units for formation of pyridine moiety of indolizines, allyl bromides easily derived from Morita-Baylis-Hillman (MBH) adducts were employed. We found that positioning electron-withdrawing group(s) at the aromatic ring of allyl bromides was a key to successful ring closure to allow access to indolizines with unique substitution style. Structurally relevant imidazo[1,2-a]pyridine and pyrido[1,2-a]indole were assembled by this method as well.

Original languageEnglish
Pages (from-to)1982-1991
Number of pages10
JournalTetrahedron
Volume71
Issue number13
DOIs
Publication statusPublished - 2015 Apr 1

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Indolizines
Electrons
Substitution reactions
Carbon
allyl bromide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach. / Park, Sujin; Kim, Ikyon.

In: Tetrahedron, Vol. 71, No. 13, 01.04.2015, p. 1982-1991.

Research output: Contribution to journalArticle

TY - JOUR

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AB - A new synthetic approach to 6,7-disubstituted indolizines has been developed from pyrrole-2-carboxaldehydes and allyl bromides via two successive base-mediated reactions. As three-carbon units for formation of pyridine moiety of indolizines, allyl bromides easily derived from Morita-Baylis-Hillman (MBH) adducts were employed. We found that positioning electron-withdrawing group(s) at the aromatic ring of allyl bromides was a key to successful ring closure to allow access to indolizines with unique substitution style. Structurally relevant imidazo[1,2-a]pyridine and pyrido[1,2-a]indole were assembled by this method as well.

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