A palladium-catalyzed facile and general method for the stereoselective synthesis of (E)-3-arylidene-3,4-dihydro-2H-1,4-benzoxazines and their naphthoxazine analogues
A palladium-catalyzed facile and general method for the stereoselective synthesis of (E)-3-arylidene-3,4-dihydro-2H-1,4-benzoxazines and their naphthoxazine analogues
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DOI：
10.1016/j.tet.2014.06.036
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发表时间：
2014-09-02
期刊：
影响因子：
2.1
通讯作者：
Chowdhury, Chinmay
中科院分区：
文献类型：
--
作者：
Brahma, Kaushik;Das, Bimolendu;Chowdhury, Chinmay
钯催化的芳基碘化物与 N-甲苯磺酰基-2-(丙-2'-炔氧基)苯胺在室温下的环缩合被证明是合成 (E)-3-亚芳基-3,4-二氢-2H-1,4-苯并恶嗪的一种方便的通用方法，收率中等至非常高。该方法还可以扩展到(E)-3-亚芳基-2H-萘[1,2-b][1,4]恶嗪的合成。该过程的区域和立体选择性、反应时间短、操作简单以及使用廉价的起始材料代表了其有吸引力的特征。 (C) 2014 Elsevier Ltd. 保留所有权利。
Palladium-catalyzed cyclocondensation of an aryl iodide with N-tosyl-2-(prop-2'-ynyloxy)aniline at room temperature is shown to constitute a convenient general method for the synthesis of (E)-3-arylidene-3,4-dihydro-2H-1,4-benzoxazines in moderate to very good yields. The method could also be extended to the synthesis of (E)-3-arylidene-2H-naphth[1,2-b][1,4]oxazines. The regio- and stereo-selectivity of the process, short reaction time, operational simplicity, and use of inexpensive starting materials represent its attractive features. (C) 2014 Elsevier Ltd. All rights reserved.