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

Autor: Maria Joaquina Vieira, Aderson de Farias Dias, Alfredo Mayall Simas, Joseph Miller, Petrônio Filgueiras de Athayde Filho, Bruno Freitas Lira
Jazyk: angličtina
Rok vydání: 2002
Předmět:
Zdroj: Molecules, Vol 7, Iss 11, Pp 791-800 (2002)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/71100791
Popis: 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.
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