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Facile and regioselective synthesis of functionalized benzenes via cascade reactions of 1,2-allenic ketones with 4-sulfonyl crotonates

Author:
Duan, Shitao, Xu, Yuanshuang, Zhang, Xinying, Fan, Xuesen
Source:
Tetrahedron 2018
ISSN:
0040-4020
Subject:
aldehydes, aromatization, benzene, chemical structure, ketones, regioselectivity
Abstract:
An efficient and regioselective synthesis of functionalized benzenes via the cascade reactions of 1,2-allenic ketones with 4-sulfonyl crotonates under mild reaction conditions has been established. Mechanistically, the formation of the title compounds involves a cascade procedure consisting of an intermolecular regioselective Michael addition followed by an intramolecular condensation and aromatization. Compared with those of α,β-unsaturated aldehydes/ketones, the reactions of 1,2-allenic ketones with 4-sulfonyl crotonates demonstrated contrary regio-selectivity and distinct reaction conditions. Moreover, the functionalized benzene products obtained herein were found to be ready intermediates for the synthesis of fluorenone and anthracenone derivatives.
Agid:
6018077