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

页码：2099 / 2105

页数：7

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