Metal- and Oxidant-Free Synthesis of Quinazolinones from β-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage

The Journal of Organic Chemistry
Zhongwen LiShuang-Feng Yin

Abstract

A general and efficient phosphorous acid-catalyzed cyclocondensation of β-ketoesters with o-aminobenzamides via selective C-C bond cleavage leading to quinazolinones is developed. This reaction proceeds smoothly under metal- and oxidant-free conditions, giving both 2-alkyl- and 2-aryl-substituted quinazolinones in excellent yields. This strategy can also be applied to the synthesis of other N-heterocycles, such as benzimidazoles and benzothiazoles.

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Citations

Jul 20, 2017·The Journal of Organic Chemistry·Wong PhakhodeeMookda Pattarawarapan
Feb 14, 2019·Organic & Biomolecular Chemistry·Fangpeng HuGuosheng Huang
Nov 7, 2019·Organic & Biomolecular Chemistry·Imran Kazi, Govindasamy Sekar
Feb 1, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Xin ZhangHe-Gen Zheng
Nov 15, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joshua T GavinRichard A Bunce
Feb 3, 2018·Organic & Biomolecular Chemistry·Saurabh SharmaPralay Das
Sep 17, 2020·Organic & Biomolecular Chemistry·Guo-Ping YangYu-Feng Liu
Dec 27, 2019·The Journal of Organic Chemistry·Shaofeng WuYongbo Zhou
Aug 7, 2018·The Journal of Organic Chemistry·Tian-Yang YuHao Wei

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