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2022 , Vol. 42 >Issue 3: 854 - 862

DOI: https://doi.org/10.6023/cjoc202109014

研究论文

I2/PhNO2介导的芳乙酮C(CO)—C键氧化断裂和2-氨基芳甲酰胺胺化合成喹唑啉-4(3H)-酮

  • 张瑞芹 ,
  • 马仁超 ,
  • 傅琴姣 ,
  • 陈静 ,
  • 马永敏
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  • a 浙江中医药大学药学院 杭州 310053
    b 台州学院高等研究院 浙江台州 318000
† 共同第一作者

收稿日期: 2021-09-07

  修回日期: 2021-10-14

  网络出版日期: 2021-11-03

基金资助

浙江省自然科学基金(LY19H300001)

收起

I2/PhNO2 Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides

  • Ruiqin Zhang ,
  • Renchao Ma ,
  • Qinjiao Fu ,
  • Jing Chen ,
  • Yongmin Ma
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  • a School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou 310053
    b School of Advanced Study, Taizhou University, Taizhou, Zhejiang 318000
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;

Received date: 2021-09-07

  Revised date: 2021-10-14

  Online published: 2021-11-03

Supported by

Zhejiang Provincial Natural Science Foundation of China(LY19H300001)

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摘要

开发了一种以苯乙酮和2-氨基苯甲酰胺为原料, 在I2/PhNO2介导下合成了喹唑啉-4(3H)-酮的新方法. 该反应涉及苯乙酮与2-氨基苯甲酰胺间的两个C—N键的形成, 接着苯乙酮的C(CO)—C键氧化裂解. 此外, 还进行了由I2/PhNO2和CuBr/K2CO3介导的一锅串联合成喹唑啉-4(3H)-酮的反应.

关键词： C(CO)—C键断裂; 喹唑啉酮; 碘; 环合; 氧化

本文引用格式

张瑞芹 , 马仁超 , 傅琴姣 , 陈静 , 马永敏 . I2/PhNO2介导的芳乙酮C(CO)—C键氧化断裂和2-氨基芳甲酰胺胺化合成喹唑啉-4(3H)-酮[J]. 有机化学, 2022 , 42(3) : 854 -862 . DOI: 10.6023/cjoc202109014

Abstract

A simple and efficient protocol for the synthesis of quinazolin-4(3H)-ones from acetophenones and 2-aminobenz- amides mediated by I2/PhNO2 has been achieved. The reaction probably involves two C—N bond formations between acetophenones and 2-aminobenzamides followed by C(CO)—C bond oxidative cleavage of acetophenones. Alternatively, a one-pot tandem reaction mediated by I2/PhNO2 and CuBr/K2CO3 was performed for the synthesis of quinazolin-4(3H)-ones.

Key words： C(CO)—C cleavage; quinazolinone; iodine; annulation; oxidation

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