Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides

doi:10.6023/cjoc202101044

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2175-2187.DOI: 10.6023/cjoc202101044 Previous Articles Next Articles

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基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展

杨凯^a^,^b, 刘美娟^a, 张毓娜^a, 占佳琦^a, 邓璐璇^a, 郑雪洁^a, 周永军^a, 汪朝阳^a^,^*()

a 华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医药分析化学重点实验室广州 510006
b 赣南医学院药学院江西赣州 341000

收稿日期:2021-01-26 修回日期:2021-02-20 发布日期:2021-03-04
通讯作者: 汪朝阳
基金资助:
广州市科技计划科学研究专项(201607010251); 广东省科技计划(2017A010103016); 江西省教育厅科学技术研究(GJJ201504); 赣南医学院(YB201903); 广东省大学生创新创业训练计划(S202010574059)

Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides

Kai Yang^a^,^b, Meijuan Liu^a, Yu'na Zhang^a, Jiaqi Zhan^a, Luxuan Deng^a, Xuejie Zheng^a, Yongjun Zhou^a, Zhaoyang Wang^a()

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
b College of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received:2021-01-26 Revised:2021-02-20 Published:2021-03-04
Contact: Zhaoyang Wang
Supported by:
Guangzhou Science and Technology Project Scientific Special(201607010251); Guangdong Provincial Science and Technology Project(2017A010103016); Scientific Research Fund of Jiangxi Provincial Education Department(GJJ201504); Gannan Medical University(YB201903); Undergraduates Innovation Project of Guangdong Province(S202010574059)

Owing to important pharmacological and biological activities of benzoheterocyclic compounds, their exploration for efficient synthesis methods in drug field is of great value and wide application. Due to the existence of multiple functional groups and reaction sites, great progress has been made in the synthesis of quinazolinones, isoquinolinones, isoindolinones, benzisothiazolones and other benzoheterocyclic compounds using 2-halobenzamides as important synthons. In view of this, according to the different structures of the products, the research progress in the synthesis of benzoheterocyclic compounds with 2-halobenzamides as the starting material in recent 10 years is summarized, and the related reaction mechanism is expounded.

Key words: 2-halobenzamide, metal catalysis, domino reaction, cyclization reaction, benzoheterocyclic compound, reaction mechanism

Cite this article

Kai Yang, Meijuan Liu, Yu'na Zhang, Jiaqi Zhan, Luxuan Deng, Xuejie Zheng, Yongjun Zhou, Zhaoyang Wang. Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2175-2187.

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Fig. & Tab. 16

Figure 1. Natural products and drug molecules with benzoheterocyclic compounds

Scheme 1. Retrosynthetic analysis for the synthesis of quinazolinones from 2-halobenzamides

Scheme 2. Copper catalyzed synthesis of quinazolinone derivatives

Scheme 3. 2-Arylquinazolinones were synthesized from 2-halobenzamides and benzylamines

Scheme 4. Synthesis of quinazolinones from 2-halobenzamides and α-amino acids

Scheme 5. Synthesis of quinazolinones from 2-halobenzamides and enaminones

Scheme 6. Synthesis of quinazolinones from 2-halobenzamides and amides

Scheme 7. Synthesis of quinazolinones from 2-halobenzamides and sodium azide

Scheme 8. Retrosynthetic analysis for the synthesis of isoquinolinones from 2-halobenzamides

Scheme 9. Reaction mechanism of Ni catalyzed 2-fluoro- benzamides with alkynes

Scheme 10. Palladium-catalyzed synthesis of phenanthridinones from o-halobenzamides

Scheme 11. Pd-Catalyzed coupling of o-bromobenzamides

Scheme 12. CuI/L-proline catalyzed domino reaction of 2-bromobenzamide and terminal alkynes

Scheme 13. Preparation of benzoisothiazolones

Scheme 14. Synthesis of benzisoselenazole-3(2H)-ones from 2-bromobenzoamides and potassium thiocyanate

Scheme 15. Synthesis of dibenzoxazepinones

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基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展

Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides

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