An Efficient Synthesis of a Highly Functionalized Dihydrobenzothiophene Derivative: A Ring-Contracted Analogue of the Anti-inflammatory Drug Propoxicam

Giammarco Tenti,Jose Clerigue,M. Teresa Ramos,J. Carlos Menendez

Synlett（2022）

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摘要

A five-step route to a ring-contracted analogue of the oxicam derivative propoxicam from thiosalicylic acid, sarcosine and N,N-dimethyl-1,3-propanediamine is described. The route has as key steps the base-promoted cross-Claisen coupling of protected sarcosine and thiosalicylic acid derivatives, the installation of a beta-ketoamide moiety and a final Hg(II)-induced cyclization that creates the C-S bond of the benzothiophen-3-one core.

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oxicam,benzotriazole activation,cross-Claisen coupling,beta-ketoamide synthesis,benzothiophene synthesis,domino reactions

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An Efficient Synthesis of a Highly Functionalized Dihydrobenzo­thiophene Derivative: A Ring-Contracted Analogue of the Anti-inflammatory Drug Propoxicam

An Efficient Synthesis of a Highly Functionalized Dihydrobenzothiophene Derivative: A Ring-Contracted Analogue of the Anti-inflammatory Drug Propoxicam