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Revista de Chimie (Rev. Chim.), Year 2008, Volume 59, Issue 11,

https://doi.org/10.37358/RC.08.11.2013

Valentin Zaharia, Anca Silvestru, Philippe Verite, Mircea Vlassa, Silvia Imre, Cristian Silvestru

Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

Abstract:

The condensation reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone was performed in basic catalysis, resulting in a mixture of 2,3-epoxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-propan-1-one (1), 1-phenyl-3-(2-phenyl-thiazol-4-yl)-propane-1,2-dione (2) and 2-phenyl-4,5-bis-(2-phenyl-thiazol-4-yl)-3-hydroxy-furane (4). The isolated solids were structurally investigated by spectroscopic methods, i.e. infrared spectroscopy, mass spectrometry and NMR. In solution the dicarbonylic derivative 2 undergoes a tautomeric process, resulting in the enol 2-hydroxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-prop-2-en-1-one 3. Compounds 3 and 4 were transformed in the corresponding acetyl derivatives 5 and 6, respectively, by reacting them with acetic anhydride. For the furane 4 the single crystal X-ray diffraction structure was determined.

Keywords:
condensation reaction; thiazol derivatives; keto - enolic tautomerism

Issue: 2008, Volume 59, Issue 11
Pages:
Publication date: 2008/10/9
https://doi.org/10.37358/RC.08.11.2013
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