The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from Donor-Acceptor Cyclopropanes

被引：9
|
作者：
Smith, Robert J. [1 ]
Mills, Daniel A. [1 ]
Nhu, Duong [1 ]
Tan, Eng Wui [1 ]
Lucas, Nigel T. [1 ]
Hawkins, Bill C. [1 ]
机构：
[1] Univ Otago, Dept Chem, POB 56, Dunedin, New Zealand
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 05期
关键词：
HETEROCYCLES; IMINES; 2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE; 2,3-DIHYDRO-1,3-OXAZIN-4-ONES; REARRANGEMENT; ACYLKETENES;
D O I：
10.1021/acs.joc.6b00112
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of electronically diverse imines were found to readily react with various donor-acceptor cyclopropyl acid chlorides, with complete regioselectivity, to form 1,3-oxazin-4-ones in moderate yields (25-48% over two steps). Select oxazinones underwent a base induced rearrangement to afford the corresponding cycloheptene-fused oxazinones in good yields (up to 70%).
引用
收藏
页码：2099 / 2105
页数：7
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