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Metal-Free Annulative Hydrosulfonation of Propiolate Esters: Synthesis of 4-Sulfonates of Coumarins and Butenolides

Abstract

An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.

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Article information


Submitted
29 Dec 2019
Accepted
14 Feb 2020
First published
14 Feb 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

Metal-Free Annulative Hydrosulfonation of Propiolate Esters: Synthesis of 4-Sulfonates of Coumarins and Butenolides

R. A. Fernandes, A. J. Gangani and R. A. Kunkalkar, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ06438A

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