Cycloaddition reactions of phosphorylated 1,2-diaza-1,3-butadienes with olefins:: Regioselective synthesis of pyridazine derivatives

被引：37
|
作者：
Palacios, F [1 ]
Aparicio, D [1 ]
López, Y [1 ]
Santos, JMD [1 ]
Alonso, C [1 ]
机构：
[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Vitoria 01080, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 06期
关键词：
cycloadditions; diazabutadienes; hydrazones; fused-ring systems; nitrogen heterocycles;
D O I：
10.1002/ejoc.200400675
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The aza-Diels-Alder reaction of 4-phosphinyl- and 4-phosphonyl-1,2-diaza-1,3-butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported. Monocyclic, bicyclic and polycyclic tetrahydropyridazines containing a phosphane oxide or a phosphonate substituent are obtained. The formation of cycloadducts can be explained by an endo transition state in the cycloaddition process of these heterodienes with styrene, cyclopentadiene, dihydrofuran, and by means of an exo transition state in the case of norbornadiene. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheirn, Germany, 2005).
引用
收藏
页码：1142 / 1147
页数：6
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