First regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles

[Display omitted] The regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles is described for the first time. The iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles using molecular iodine afforded diiodo-compound which on CuI-catalyzed intramo...

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Bibliographic Details
Published in:Tetrahedron letters 2015-09, Vol.56 (36), p.5140-5144
Main Authors: Rode, Navnath D., Sonawane, Amol D., Garud, Dinesh R., Joshi, Rohini R., Joshi, Ramesh A., Likhite, Anjali P.
Format: Article
Language:English
Subjects:
Iodocyclization
Regioselective
Thiazine
Triazole
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Summary:[Display omitted] The regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles is described for the first time. The iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles using molecular iodine afforded diiodo-compound which on CuI-catalyzed intramolecular C–N coupling reaction gave six-membered 2-aryl-5H-[1,2,4]triazolo[5,1-b][1,3]thiazines, whereas, the five membered 3-aryl-5,6-dihydrothiazolo[2,3-c][1,2,4]triazoles were obtained exclusively when the iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles was carried out using NIS.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.07.006