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Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective Iodocyclization of Ynamides

Author:
Huang, Hai, Zhu, Xiaolin, He, Guangke, Liu, Qi, Fan, Junzhen, Zhu, Hongjun
Source:
Organic letters 2015 v.17 no.10 pp. 2510-2513
ISSN:
1523-7052
Subject:
acetonitrile, chemical reactions, chemical structure, regioselectivity, solvents
Abstract:
Two efficient processes based on the iodocyclization of ynamides have been developed: (i) N-alkynyl tert-butyloxycarbamates were found to undergo a rare 6-exo-dig ring closure reaction affording 1,3,5-oxadiazin-2-ones by using acetonitrile as solvent; (ii) In the absence of acetonitrile, N-alkynyl tert-butyloxycarbamates could undergo 5-endo-dig cyclization providing oxazolones.
Agid:
5788718