Stereoselective synthesis of fused heterocycles from substituted o-Benzoquinones and anilines |
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Authors: | Yu A Kurskii N O Druzhkov T N Kocherova A S Shavyrin V K Cherkasov G A Abakumov |
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Institution: | 1. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, ul. Tropinina 49, Nizhni Novgorod, 603950, Russia
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Abstract: | The reaction of trisubstituted o-benzoquinones with substituted anilines gives unstable o-benzoquinone imines which undergo intramolecular cyclization to 4aH-phenoxazine derivatives. Dimerization of the latter according to Diels-Alder yields complex heterocyclic systems, 7a,14a,15a,15b-tetrahydro-14,16-dioxa-5,9-diaza-8,15-ethenohexaphenes. Effective shielding of the carbonyl groups in 3,6-di-tert-butyl-4-isopropyl-o-benzoquinone makes it inactive toward substituted anilines. |
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