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An Inverse Electron Demand Azo-Diels-Alder Reaction of o-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines

Dmitry V. Osipov, Vitaly A. Osyanin*, Guzel' D. Khaysanova, Elvira R. Masterova, Pavel E. Krasnikov and Yuri N. Klimochkin

*Department of Organic Chemistry, Chemical Technological Faculty, Samara State Technical University, 244 Molodogvardeyskaya Street, Samara 443100, Russian Federation, Email: vosyaninmail.ru

D. V. Osipov, V. A. Osyanin, G. D. Khaysanova, E. R. Masterova, P. E. Krasnikov, Y. N. Klimochkin, J. Org. Chem., 2018, 83, 4775-4785.

DOI: 10.1021/acs.joc.8b00692 (free Supporting Information)


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Abstract

The reaction of o-quinone methide precursors with imino ethers provides a versatile route to substituted 1,3-benzoxazines via imino-Diels-Alder reaction and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.


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Key Words

benzo fused O-heterocycles, benzo fused N-heterocycles, Diels-Alder reaction


ID: J42-Y2018