Preparation of Some heterocyclic enones and ynones by isomerisation of the propargylic alcohols-Reference-Cited by-同舟云学术

Preparation of Some heterocyclic enones and ynones by isomerisation of the propargylic alcohols

Published:2009-07 Issue:7 Volume:2009 Page:459-464
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Erenler Ramazan¹²,Uno Masaharu³,Goud Thirumani Venkateshwar¹,Biellmann Jean-François¹

Affiliation:

1. Institute of Chemistry, Academia Sinica, Nankang 115, Taipei, Taiwan

2. Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University 60240 Tokat, Turkey

3. Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan

Abstract

The propargylic alcohols were synthesised by treatment of aldehydes with substituted acetylenes. The conversion of propargylic alcohols to propynones and propenones takes place with pyridine hydrochloride in methanol at room temperature. In presence of pyridinium triflate and p-toluenesulfonate the propynone was the only product isolated in the isomerisation of alcohol. The silylated propenone undergoes with cyclopentadiene a Diels–Alder cycloaddition to give ketone whose skeleton is related to that of quinine.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823409X464467

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