Tunable Synthesis of Functionalized Cyclohexa-1,3-dienes and 2-Aminobenzophenones/Benzoate from the Cascade Reactions of Allenic Ketones/Allenoate with Amines and Enones.

J Org Chem

School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education , Henan Normal University, Xinxiang , Henan 453007 , China.

Published: May 2018

A TEMPO-dependent tunable synthesis of functionalized cyclohexa-1,3-dienes and 2-aminobenzophenones/benzoate from the one-pot cascade reactions of allenic ketones/allenoate with amines and enones is presented. Mechanistically, the construction of the entitled six-membered carbocycles involves the in situ generation of an enaminone intermediate via the conjugate addition of allenic ketone with amine followed by its catalyst- and base-free [3+3] annulation with enone along with the simultaneous introduction of the valuable amino and carbonyl groups.

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http://dx.doi.org/10.1021/acs.joc.8b00473DOI Listing

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