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

We have studied the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels–Alder reaction, and elimination. This...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-04, Vol.83 (8), p.4775-4785
Main Authors: Osipov, Dmitry V, Osyanin, Vitaly A, Khaysanova, Guzel’ D, Masterova, Elvira R, Krasnikov, Pavel E, Klimochkin, Yuri N
Format: Article
Language:English
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Summary:We have studied the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels–Alder reaction, and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00692