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

被引：44

作者：

Huang, Hai ^{[1
]}

Zhu, Xiaolin ^{[1
]}

He, Guangke ^{[1
]}

Liu, Qi ^{[1
]}

Fan, Junzhen ^{[1
]}

Zhu, Hongjun ^{[1
]}

机构：

[1] Nanjing Tech Univ, Coll Sci, Dept Appl Chem, Nanjing 211816, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 10期

关键词：

ELECTROPHILIC CYCLIZATION; MEDIATED CYCLIZATION; MOLECULAR-IODINE; DERIVATIVES; IODOCYCLIZATION; ARYL; HETEROCYCLES; HALIDES; AMIDES; ALKYNE;

D O I：

10.1021/acs.orglett.5b01045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2510 / 2513

页数：4

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