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

Molecules

Bruno Freitas Lira²  Petrônio Filgueiras de Athayde Filho²  Joseph Miller²  Alfredo Mayall Simas¹  Aderson de Farias Dias² 

[1] Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50.670-901, Recife-PE, Brasil;Laboratório de Tecnologia Farmacêutica and ² Departamento de Química, Universidade Federal da Paraíba, 58.051-970, João Pessoa-PB, Brasil; ^†

关键词: Mesoionic 1;    3-thiazolium-5-thiolates;    Synthesis;    Characterization;   

DOI  :  10.3390/71100791

来源: mdpi

【 摘 要 】

The title compounds were synthesized from C-aryl-N-methylglycines by N-aroylation 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-dicyclohexyl-carbodiimide (DCC) at temperatures not exceding 60^oC. 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.

【 授权许可】

Unknown   
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