l-Proline-Catalyzed Three-Component Reaction of 4-Chloro-3-formylcoumarin, Sodium Sulfide, and α-Halo Ketones: A Direct Approach to Thieno[3,2-c]coumarins

Dedicated to Professor Hala S. Al-Easa of Qatar university on the occasion of her retirement.

Abstract

A new protocol for the synthesis of thieno[3,2-c]coumarins is disclosed. In this method, a 3-formyl-2-oxo-2H-chromene-4-thiolate anion is generated in situ by treatment of 4-chloro-3-formylcoumarin with sodium sulfide. This chromene-4-thiolate undergoes an l-proline-catalyzed substitution/Knoevenagel cascade with various α-halo ketones to afford the desired thienocoumarins in moderate to good isolated yields. This protocol eliminates the need for stoichiometric amounts of inorganic bases and the use of foul-smelling thiols. The reaction conditions tolerate a variety of α-halo ketones.

Key words

organocatalysis - multicomponent reaction - thienocoumarins - thiophene - proline catalysis - cascade reaction

Publication History

Received: 13 October 2022

Accepted after revision: 27 November 2022

Accepted Manuscript online:
27 November 2022

Article published online:
10 January 2023

• References and Notes

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