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Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazoles

Tryfon Zarganes-Tzitzikas, Constantinos G. Neochoritis, Julia Stephanidou-Stephanatou, Constantinos A. Tsoleridis, Gernot Buth, Kostakis Georgios

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URIhttp://purl.tuc.gr/dl/dias/C1D7A97B-8880-49B4-AC9E-5A56716EB77C-
Identifierhttp://www.sciencedirect.com/science/article/pii/S0040402013004997-
Identifierhttps://doi.org/10.1016/j.tet.2013.03.096-
Languageen-
Extent8 pagesen
TitleAzodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazolesen
CreatorTryfon Zarganes-Tzitzikasen
CreatorConstantinos G. Neochoritisen
Creator Julia Stephanidou-Stephanatouen
CreatorConstantinos A. Tsoleridisen
Creator Gernot Buthen
CreatorKostakis Georgiosen
CreatorΚωστακης Γεωργιοςel
PublisherElsevieren
Content SummaryUpon reaction of 4,5-disubstituted-N-arylaminoimidazole-2-thiones with isocyanides in the presence of azodicarboxylates (1.2 equiv) at rt, the imidazo[2,1-b][1,3,4]thiadiazoles were formed as the only reaction products in very good yields, whereas by using higher reaction temperatures, along with the imidazo[2,1-b][1,3,4]thiadiazoles, the three component reaction products, namely thiadiazoles, were also isolated, their formation being dependent on the 5-thione substituent. The thiadiazoles became the only reaction products, formed in very good yield by using 2 equiv of azodicarboxylates. The sodium cyanoborohydride and sodium borohydride reductions to thiadiazoles 11, and 12 were also studied. Plausible mechanistic schemes for the formation of the thiadiazoles are proposed.en
Type of ItemPeer-Reviewed Journal Publicationen
Type of ItemΔημοσίευση σε Περιοδικό με Κριτέςel
Licensehttp://creativecommons.org/licenses/by/4.0/en
Date of Item2015-12-04-
Date of Publication2013-
SubjectAzodicarboxylatesen
SubjectIsocyanidesen
SubjectThionesen
SubjectImidazo[2,1-b][1,3,4]thiadiazolesen
SubjectMulticomponent reactionsen
SubjectThiadiazolesen
Bibliographic CitationT. Zarganes-Tzitzikas, C. G. Neochoritis, J. Stephanidou-Stephanatou, C. A. Tsoleridis, G. Buth, and G. E. Kostakis, "Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazoles", Tetrahedron, vol. 69, no. 24, pp. 5008-5015, Jun. 2013. doi:10.1016/j.tet.2013.03.096en

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