[4+2] Cycloaddition of 1-phosphono-1,3-butadiene with azo- and nitroso-heterodienophiles

被引：22
|
作者：
Monbaliu, Jean-Christophe [1 ]
Marchand-Brynaert, Jacqueline [1 ]
机构：
[1] Catholic Univ Louvain, Dept Chim, Unite Chim Organ & Med, B-1348 Louvain, Belgium
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 11期
关键词：
hetero Diels-Alder reaction; 1-phosphono-1,3-butadiene; azo dienophile; nitroso dienophile; microwave activation; aminophosphonic derivatives;
D O I：
10.1016/j.tetlet.2008.01.050
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Under microwave activation, diethyl 1-phosphono-1,3-butadiene (1) reacted with t-butyl azodicarboxylate (2) and o-nitrosotoluene (5) to furnish quantitatively [4+2] cycloadducts, 3-phosphono-3,6-dihydro-1,2-pyridazine (3) and 6-phosphono-3,6-dihydro-1,2-oxazine (6), respectively. Selective oxidation and/or reduction of 6 led to functionalized 6-aminophosphonic derivatives in cyclic (7, 8) and aliphatic series (9, 10). Intermediate 10 may be cyclized into 2-phosphono-2,5-dihydro-1-pyrrole (12). (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1839 / 1842
页数：4
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