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

页码：4061 / 4064

页数：4

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