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

doi:10.1007/s40242-024-4078-5

高等学校化学研究 ›› 2024, Vol. 40 ›› Issue (6): 1212-1219.doi: 10.1007/s40242-024-4078-5

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

XU Jianxiong, HUANG Weimin, LI Jizhen

College of Chemistry, Jilin University, Changchun 130021, P. R. China

收稿日期:2024-03-29 出版日期:2024-12-01 发布日期:2024-10-26
通讯作者: LI Jizhen,ljz@jlu.edu.cn;HUANG Weimin,huangwm@jlu.edu.cn E-mail:ljz@jlu.edu.cn;huangwm@jlu.edu.cn
基金资助:
This work was supported by the Open Funds of the State Key Laboratory of Rare Earth Resource Utilization, China (No. RERU2023006).

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

XU Jianxiong, HUANG Weimin, LI Jizhen

College of Chemistry, Jilin University, Changchun 130021, P. R. China

Received:2024-03-29 Online:2024-12-01 Published:2024-10-26
Contact: LI Jizhen,ljz@jlu.edu.cn;HUANG Weimin,huangwm@jlu.edu.cn E-mail:ljz@jlu.edu.cn;huangwm@jlu.edu.cn
Supported by:
This work was supported by the Open Funds of the State Key Laboratory of Rare Earth Resource Utilization, China (No. RERU2023006).

摘要/Abstract

摘要： 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.

关键词: Ethyl acetate, Acylation, Chlorine radical, N-Heteroarene, Minisci-type

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]. 高等学校化学研究, 2024, 40(6): 1212-1219.

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

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

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