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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
1 Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, 58.051-970, João Pessoa-PB, Brasil 2 Departamento de Química, Universidade Federal da Paraíba, 58.051-970, João Pessoa-PB, Brasil 3 Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50.670-901, Recife- PE, Brasil 4 Universidade Federal da Paraíba, Departamento de Ciências Básicas Sociais, 58.220-000, Bananeiras- PB, Brasil
* Author to whom correspondence should be addressed.
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
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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