4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 41, Pages 5419-5422

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.07.172

Keywords

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Funding

  1. EPSRC
  2. Cardiff OH University
  3. Engineering and Physical Sciences Research Council [EP/I006052/1] Funding Source: researchfish
  4. EPSRC [EP/I006052/1] Funding Source: UKRI

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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.

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