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Molecules 2002, 7(11), 791-800; doi:10.3390/71100791
Article

Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion

1,3, 2,4, 1,2,3,* , 3, 1
 and
2
Received: 25 February 2002 / Revised: 11 November 2002 / Accepted: 14 November 2002 / Published: 30 November 2002
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Abstract

The title compounds were synthesized from C-aryl-N-methylglycines by Naroylation followed by a cyclodehydration to form the corresponding 1,3-oxazolium-5-olates. These were not isolated but converted to the title compounds by an in situ 1,3-dipolar cycloaddition/cycloreversion sequence using carbon disulphide. We have studied the cyclodehydration step using acetic anhydride, trifluoroacetic anhydride and 1,3-dicyclohexylcarbodiimide (DCC) at temperatures not exceding 60oC. Trifluroacetic anhydride proved to be the best reagent, giving a better yield and more easily purified products, although yields were also acceptable with the other two reagents.
Keywords: Mesoionic 1; 3-thiazolium-5-thiolates; Synthesis; Characterization Mesoionic 1; 3-thiazolium-5-thiolates; Synthesis; Characterization
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Lira, B.F.; De Athayde Filho, P.F.; Miller, J.; Simas, A.M.; De Farias Dias, A.; Vieira, M.J. Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion. Molecules 2002, 7, 791-800.

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