Iodine-promoted cyclization of N-propynyl amides and N-allyl amides via sulfonylation and sulfenylation

An iodine-promoted regioselective cyclization of N-propynyl/allyl amides with sulfonyl hydrazides has been developed for the synthesis of 5-methyl-arylsulfonyloxazoles and 5-methyl-arylthiooxazolines via sulfonylation and sulfenylation reactions. The notable features of this reaction are the formati...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (76), p.11410-11413
Main Authors: Senadi, Gopal Chandru, Guo, Bing-Chun, Hu, Wan-Ping, Wang, Jeh-Jeng
Format: Article
Language:English
Subjects:
Alkynes
Amides
Chemical bonds
Formations
Functional groups
Hydrazides
Synthesis (chemistry)
Tolerances
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Summary:An iodine-promoted regioselective cyclization of N-propynyl/allyl amides with sulfonyl hydrazides has been developed for the synthesis of 5-methyl-arylsulfonyloxazoles and 5-methyl-arylthiooxazolines via sulfonylation and sulfenylation reactions. The notable features of this reaction are the formation of new C-S and C-O bonds, the broad functional group tolerance, and its applicability to alkyl sulfonyl hydrazides as well as internal alkynes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc05138c