Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones.

J Org Chem

Institute of Functional Organic Molecular Engineering, Henan Engineering Laboratory of Flame-Retardant and Functional Materials, College of Chemistry and Chemical Engineering , Henan University, Kaifeng 475004 , China.

Published: June 2019

Effective transition-metal-free formal [4+2] benzannulation for the preparation of 1-cyano-3-acylnaphthalenes from 2-(2-alkynylphenyl)acetonitriles and alkynones through sequential C-C bond coupling has been developed. This protocol is characterized by mild conditions, excellent functional group tolerance, complete regioselectivity, and atom economy. The plausible mechanism, gram-scale synthesis, and further transformations of the product were studied.

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http://dx.doi.org/10.1021/acs.joc.9b00948DOI Listing

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