The diene-transmissive hetero-Diels-Alder reaction of 2-vinyl α,β-unsaturated aldimines: stereoselective synthesis of hexahydroquinazolin-2-ones.
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.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan. tsaito@rs.kagu.tus.ac.jp.
Satoru
S
Kobayashi
Kenji
K
Kudo
Ai
A
Ito
Satoru
S
Hirama
Takashi
T
Otani
Takao
T
Saito