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

Bruno Freitas Lira 1,3 , Petrônio Filgueiras De Athayde Filho 2,4 , Joseph Miller 1,2,3,* email, Alfredo Mayall Simas 3 , Aderson De Farias Dias 1 email and Maria Joaquina Vieira 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; in revised form: 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

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Cite This Article

MDPI and ACS Style

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.

AMA Style

Lira BF, De Athayde Filho PF, Miller J, Simas AM, De Farias Dias A, Vieira MJ. 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(11):791-800.

Chicago/Turabian Style

Lira, Bruno F.; De Athayde Filho, Petrônio F.; Miller, Joseph; Simas, Alfredo M.; De Farias Dias, Aderson; Vieira, Maria J. 2002. "Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion." Molecules 7, no. 11: 791-800.

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