TMSCl-catalyzed aza-Diels-Alder reaction: A simple and efficient synthesis of pyrano- and furanoquinolines

Shivaji V. More, M. N.V. Sastry, Ching Fa Yao

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

Original languageEnglish
Pages (from-to)1399-1403
Number of pages5
JournalSynlett
Issue number9
DOIs
Publication statusPublished - 2006 Jun 1

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Aniline Compounds
Aldehydes
Reaction rates
Derivatives
Temperature
2,3-dihydrofuran
3,4-dihydro-(2H)-pyran

Keywords

  • Excellent yields
  • One-pot
  • Pyrano- and furanoquinolines
  • TMSCl
  • aza-Diels-Alder reaction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

TMSCl-catalyzed aza-Diels-Alder reaction : A simple and efficient synthesis of pyrano- and furanoquinolines. / More, Shivaji V.; Sastry, M. N.V.; Yao, Ching Fa.

In: Synlett, No. 9, 01.06.2006, p. 1399-1403.

Research output: Contribution to journalArticle

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