Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to N-cinnamoyl piperidines-first report of the novel formation of 2:1 cycloadducts

被引：13
作者：
Banerji, A
Bandyopadhyay, D
Prangé, T
Neuman, A
机构：
[1] Univ Calcutta, Dept Chem, Ctr Adv Studies Nat Prod Organ Synth, Kolkata 700009, W Bengal, India
[2] Ctr Univ Paris Sud, F-91898 Orsay, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 15期
关键词：
nitrone; dipolar cycloaddition; intermolecular; isoxazolooxazines;
D O I：
10.1016/j.tetlet.2005.02.083
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of unexpected cycloadclucts along with normal cycloadducts have been isolated from the 1,3-dipolar cycloaddition of 3,4-clehydromorpholine N-oxide to piperidides of cinnamic acid and para-substituted cinnamic acids and these were analyzed by X-ray crystallography to reveal novel solid-state structures. At first, 1: 1 cycloadclucts were formed which underwent in situ nucleophilic attack by another reduced nitrone moiety. A plausible iminium-oxonium ion mechanism has been proposed. (c) 2005 Elsevier Ltd. All rights reserved.
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收藏
页码：2619 / 2622
页数：4
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