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[3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-­imines

Abstract : A diene-transmissive hetero-Diels–Alder reaction of cross-conjugated 1-azatrienes (3-1-azadendralenes) is described for the synthesis of hexahydroquinazolin-2-ones and hexahydrobenzothiazine-2-imines derivatives. [4+2] Cycloaddition reactions with tosyl isocyanate or aryl isothiocyanates gave mono-cycloadducts with high chemo- and regioselectivities. The second Diels–Alder reaction with representative dienophiles, tetracyanoethylene, N-phenylmaleimide, and methyl vinyl ketone, stereoselectively produced ring-fused nitrogen heterocycles. Skeletal diversity can be accessed by combining the three reaction partners – primary amine, tosyl isocyanate, and cross-conjugated 1-oxatriene – in a different sequential order
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01196571
Contributor : Laurent Jonchère <>
Submitted on : Thursday, September 10, 2015 - 10:00:12 AM
Last modification on : Thursday, July 30, 2020 - 3:11:17 AM

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Satoru Kobayashi, Kenji Kudo, Ai Ito, Takuya Honjo, Masahiro Yata, et al.. [3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-­imines. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (20), pp.4367--4373. ⟨10.1002/ejoc.201500474⟩. ⟨hal-01196571⟩

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