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

Hai Huang, Xiaolin Zhu, Guangke He, Qi Liu, Junzhen Fan, Hongjun Zhu

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

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. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)2510-2513
Number of pages4
JournalOrganic Letters
Volume17
Issue number10
DOIs
StatePublished - May 15 2015

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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