Rapid Access to Acylation and Alkylation of N-Heteroarenes Using Ester Acetates as Reactants

doi:10.1007/s40242-024-4078-5

Abstract

Abstract: The laboratory-abundant and low-toxic ethyl acetate was explored successfully for the first time as acyl group donor for the Minisci-type acylation of quinolines. In this approach, TBAC/K₂S₂O₈ (TBAC: tert-butylacetyl chloride) system played a important role, and the introduced acyl group was derived from the alkoxyl group moiety of ester acetates. Most N-heteroarenes, such as quinoxaline and isoquinoline, etc. were also compatible to this synthetic strategy affording acylated products in high yields. Simultaneously, the C2—H alkylation was realized by accident for 4-quinazolinone. Furthermore, the acylation mechanism was proposed through the chlorine radical abstracting the inactive α-hydrogen of the alkoxyl group.

Key words: Ethyl acetate, Acylation, Chlorine radical, N-Heteroarene, Minisci-type

XU Jianxiong, HUANG Weimin, LI Jizhen. Rapid Access to Acylation and Alkylation of N-Heteroarenes Using Ester Acetates as Reactants[J]. Chemical Research in Chinese Universities, 2024, 40(6): 1212-1219.

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