Reaction of Push–Pull Enaminoketones and in Situ Generated ortho-Quinone Methides: Synthesis of 3-Acyl-4H-chromenes and 2-Acyl-1H-benzo[f]chromenes as Precursors for Hydroxybenzylated Heterocycles

作者: Anton V. Lukashenko , Vitaly A. Osyanin , Dmitry V. Osipov , Yuri N. Klimochkin

DOI: 10.1021/ACS.JOC.6B02716

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摘要: A simple and efficient method for the synthesis of 4H-chromenes 1H-benzo[f]chromenes containing a trifluoroacetyl or aroyl group in pyran ring from o-quinone methide precursors push–pull enaminoketones has been developed. The chromenes are presumably formed through an initial oxa-Diels–Alder reaction, followed by elimination amine. possibility further transformations given to o-hydroxybenzylated pyrazoles, isoxazoles, pyridines demonstrated.

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