Synthesis of 1, 3, 4, 9??tetrahydro??1??alkylthiopyrano [3, 4??b] indole??1??acetic acids. The sulfur isoster of prodolic acid

I Jirkovsky, LG Humber…

Index: Jirkovsky,I. et al. Journal of Heterocyclic Chemistry, 1975 , vol. 12, p. 937 - 940

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Citation Number: 4

Abstract

Abstract The condensation of thiotryptophol with β-ketoesters and successive hydrolysis of the intermediates afforded the title compounds which represent a novel ring system. The reaction of thiotryptophol with ethyl propiolate in the presence of sodium methoxide gave the unstable 1, 3, 4, 9-tetrahydrothiopyrano [3, 4-b] indole-1-acetic acid. One of the described products is the sulfur isoster of the potent antiinflammatory agent, prodolic acid. The sulfur ...