Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones

被引：6
|
作者：
Vasu, Dhananjayan [1 ,2 ]
Leitch, Jamie A. [1 ]
Dixon, Darren J. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England
[2] Northwestern Univ, Dept Chem, Sheridan Rd, Evanston, IL 60208 USA
来源：
TETRAHEDRON | 2019年 / 75卷 / 50期
基金：
欧盟地平线“2020”;
关键词：
Benzo[1,4]oxazines; Primary amine; Heterocycle; Oxidation; AEROBIC OXIDATION; CATALYTIC-SYSTEM; QUINONE; MODEL; OXIDASES; FUNCTIONALIZATION; BENZYLAMINE; DERIVATIVES; MECHANISM;
D O I：
10.1016/j.tet.2019.130726
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The efficient oxidative construction of benzo[1,4]oxazines from simple alpha-branched amines and ortho-benzoquinones is reported. The procedure pivots on a triethylamine and iodine mediated oxidative ring closure from the ketimine intermediate formed upon their condensation. This reaction was shown to tolerate a variety of alpha-branched benzylamines and downstream derivatization to substituted benzo-morpholine structures was also demonstrated. (C) 2019 Elsevier Ltd. All rights reserved.
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页数：6
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