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 journalArticlepeer-review

18 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

Bibliographical note

Funding Information:
This research was supported in part by Nano·Material Technology Development Program through the National Research Foundation of Korea (NRF) funded by the Korean Ministry of Education, Science and Technology . This work was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) ( 2014R1A2A1A11050491 ).

Publisher Copyright:
©2015 Elsevier Ltd. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach'. Together they form a unique fingerprint.

Cite this