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

doi:10.1021/acs.orglett.5b01045

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 journal › Article › peer-review

43 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 language	English (US)
Pages (from-to)	2510-2513
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.5b01045
State	Published - May 15 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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).",

author = "Hai Huang and Xiaolin Zhu and Guangke He and Qi Liu and Junzhen Fan and Hongjun Zhu",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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day = "15",

doi = "10.1021/acs.orglett.5b01045",

language = "English (US)",

volume = "17",

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journal = "Organic Letters",

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T1 - Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective Iodocyclization of Ynamides

AU - Huang, Hai

AU - Zhu, Xiaolin

AU - He, Guangke

AU - Liu, Qi

AU - Fan, Junzhen

AU - Zhu, Hongjun

PY - 2015/5/15

Y1 - 2015/5/15

N2 - 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).

AB - 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).

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DO - 10.1021/acs.orglett.5b01045

M3 - Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

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

Abstract

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