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Issue 24, 2014
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The diene-transmissive hetero-Diels–Alder reaction of 2-vinyl α,β-unsaturated aldimines: stereoselective synthesis of hexahydroquinazolin-2-ones

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Abstract

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.

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

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Publication details

The article was received on 29 Jan 2014, accepted on 11 Mar 2014 and first published on 11 Mar 2014


Article type: Communication
DOI: 10.1039/C4OB00224E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 4061-4064
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    The diene-transmissive hetero-Diels–Alder reaction of 2-vinyl α,β-unsaturated aldimines: stereoselective synthesis of hexahydroquinazolin-2-ones

    S. Kobayashi, K. Kudo, A. Ito, S. Hirama, T. Otani and T. Saito, Org. Biomol. Chem., 2014, 12, 4061
    DOI: 10.1039/C4OB00224E

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