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

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 degrees 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. (C) 2010 Elsevier Ltd. All rights reserved.