A one-step synthesis towards new ligands based on aryl-functionalised thiazolo[5,4-d]thiazole chromophores

Knighton, Richard C., Hallett, Andrew J., Kariuki, Benson M. and Pope, Simon J.A. (2010) A one-step synthesis towards new ligands based on aryl-functionalised thiazolo[5,4-d]thiazole chromophores. Tetrahedron Letters, 51 (41), 5419-5422. (doi:10.1016/j.tetlet.2010.07.172).

Record type: Article

Abstract

A general synthesis of disubstituted thiazolo[5,4-d]thiazoles was achieved by condensing two equivalents of an aryl aldehyde with dithiooxamide in nitrobenzene at 130 °C for 24 h. The method is tolerant to a range of aromatic aldehydes including derivatives of pyridine, quinoline, mono- and dihydroxybenzene. An X-ray crystal structure of 2,5-bis(2-hydroxy-3,5-di-tert- butylphenyl)thiazolo[5,4-d]thiazole was obtained confirming the proposed formulation, together with supporting spectroscopic data that suggests that for the 2-hydroxyphenyl derivatives intramolecular hydrogen bonding exists in both solution and solid states. © 2010 Elsevier Ltd. All rights reserved.

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