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

Authors: Erenler, Ramazan; Uno, Masaharu; Goud, Thirumani Venkateshwar; Biellmann, Jean-François

Source: Journal of Chemical Research, Volume 2009, Number 7, July 2009 , pp. 459-464(6)

Publisher: Science Reviews 2000 Ltd

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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.

Keywords: ISOMERISATION; PROPARGYLIC ALCOHOL; ENONE; YNONE; HETEROCYCLIC

Document Type: Research article

DOI: http://dx.doi.org/10.3184/030823409X464467

Publication date: 2009-07-01

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The Journal of Chemical Research is a monthly journal which has a broad international authorship and publishes research papers and reviews in all branches of experimental chemistry.
Recent papers have described new synthetic methods, new heterocyclic compounds, new natural products, and the inorganic chemistry of metal complexes. Now in its 34th year, the Journal of Chemical Research was established in 1977 as a joint venture by the British, French and German chemical societies and maintains the high standards set by the founding societies. Each paper is independently peer reviewed and only carefully evaluated contributions are accepted.
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