Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Preparation of New Nitrogen-Bridged Heterocycles. 56. Syntheses and Reactions of 1-[2,2-Bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium Salts
Akikazu KakehiHiroyuki SugaYuuya YamauchiKatsuaki YasuraokaTomoshige KobayashiAkira Ohta
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2004 Volume 52 Issue 11 Pages 1316-1321


The title compounds, readily available from the S-alkylation of pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides with alkyl halides or alkyl bromoacetates, were treated with a base and then a dehydrogenating agent to provide some unique products such as 3-[bis(alkylthio)methylene]-2(3H)-indolizinones and dialkyl 7-methyl-4-oxo-1,4,8,8a-tetrahydro-1,4-thiazino[3,4,5-cd]indolizine-1,5-dicarboxylates. On the other hand, similar reaction of these pyridinium salts in the absence of the dehydrogenating agent afforded alkyl 2-hydroxyindlizine-3-carboxythiolates, whose yields were increased by adding trifluoroacetic acid to the reaction mixture. The structures of some products were confirmed by the X-ray analyses.

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© 2004 The Pharmaceutical Society of Japan
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