The diene-transmissive hetero-Diels-Alder reaction of 2-vinyl α,β-unsaturated aldimines: stereoselective synthesis of hexahydroquinazolin-2-ones

被引：12
|
作者：
Kobayashi, Satoru [1 ]
Kudo, Kenji [1 ]
Ito, Ai [1 ]
Hirama, Satoru [1 ]
Otani, Takashi [1 ]
Saito, Takao [1 ]
机构：
[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 24期
关键词：
INVERSE-ELECTRON-DEMAND; CROSS-CONJUGATED AZATRIENES; CYCLOADDITION REACTIONS; PRACTICAL SYNTHESIS; EFFICIENT; DENDRALENES; GENERATION; DIVERSITY; STRATEGY; TRIENES;
D O I：
10.1039/c4ob00224e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective synthesis of hexahydroquinazolin-2(1H)-ones has been achieved through the application of the diene-transmissive hetero-Diels-Alder methodology to 2-vinyl-1-aza-1,3-butadienes. The cross-conjugated 1-azatriene underwent an initial hetero-Diels-Alder reaction on the 1-aza-1,3-butadiene system with tosyl isocyanate to afford the [4 + 2] mono-cycloadduct pyrimidinone. The second Diels-Alder reaction on the electron-rich 1-amino-1,3-diene unit of the mono-cycloadduct with dienophiles provided hexahydroquinazolin-2(1H)-ones with high stereoselectivity.
引用
收藏
页码：4061 / 4064
页数：4
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