Straightforward synthesis of thiazolo[5,4-c]isoquinolines from dithiooxamide and 2-halobenzaldehydes?

New Journal of Chemistry Pub Date: 2022-01-20 DOI: 10.1039/D1NJ05536D

Abstract

The reaction of dithiooxamide with aromatic aldehydes is a well-known method for the preparation of thiazolo[5,4-d]thiazoles (TzTz). However, we report here that, using adequately substituted 2-halobenzaldehydes, this reaction may afford selectively thiazolo[5,4-c]isoquinolines (TzIQ) or mixtures of TzTz and TzIQ. The use of lanthanum(III) triflate as the catalyst favors the formation of TzIQ. The results obtained using a large number of substituted benzaldehydes showed that the nature, number and position of halogen atoms and other substituents on the aldehyde have a great impact on the reaction outcome. The structures of six TzTz and six TzIQ were unveiled by single-crystal X-ray diffraction.

Graphical abstract: Straightforward synthesis of thiazolo[5,4-c]isoquinolines from dithiooxamide and 2-halobenzaldehydes
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