Electrochemical Oxidation Decarboxylative Cyclization of α-Keto Acid with o-Aminobenzylamine

doi:10.6023/cjoc202310015

Abstract

A novel method for synthesizing quinazolines by an electrochemical oxidation decarboxylative cyclization reaction of α-keto acid with o-aminobenzylamine under metal and external chemical oxidants free conditions was developed. This method has mild reaction conditions, and can tolerate a wide range of functional groups, and can provide the corresponding products with moderate to excellent yields. Furthermore, the method can also be used for the synthesis of other heterocycles such as benzoxazole, benzothiazole and benzimidazole.

Key words: electrochemistry, oxidative decarboxylation, cyclization, quinazoline

Cite this article

Jiwei Wu, Jun He, Jingjing Wang, Lixia Li, Caiyu Xu, Jie Zhou, Zirong Li, Huajian Xu. Electrochemical Oxidation Decarboxylative Cyclization of α-Keto Acid with o-Aminobenzylamine[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 972-980.

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References 24

[1]	Gupta T.; Rohilla A.; Pathak A.; Akhtar J.; Haider M. R.; Yar M. S. Synth. Commun. 2018, 48, 1099. doi: 10.1080/00397911.2018.1431282
[2]	Horn K. S. V.; Burda W. N.; Fleeman R.; Shaw L. N.; Manetsch R. J. Med. Chem. 2014, 57, 3075. doi: 10.1021/jm500039e
[3]	Smits R. A.; Adami M.; Istyastono E. P.; Zuiderveld O. P.; Van Dam C. M. E.; De Kanter F. J. J.; Jongejan A.; Coruzzi G.; Leurs R.; De Esch I. J. P. J. Med. Chem. 2010, 53, 2390. doi: 10.1021/jm901379s
[4]	Madapa S.; Tusi Z.; Mishra A.; Srivastava K.; Pandey S. K.; Tripathi R.; Puri S. K.; Batra S. Bioorg. Med. Chem. 2009, 17, 222. doi: 10.1016/j.bmc.2008.11.005
[5]	Ugale V. G.; Bari S. B. Eur. J. Med. Chem. 2014, 80, 447. doi: 10.1016/j.ejmech.2014.04.072
[6]	Zhang Y.; Hou Q.; Li X.; Zhu J.; Wang W.; Li B.; Zhao L.; Xia H. Eur. J. Med. Chem. 2019, 178, 417. doi: 10.1016/j.ejmech.2019.06.015
[7]	Raskind M. A.; Peskind E. R.; Chow B.; Harris C.; Davis-Karim A.; Holmes H. A.; Hart K. L.; McFall M.; Mellman T. A.; Reist C.; Romesser J.; Rosenheck R.; Shih M. C.; Stein M. B.; Swift R.; Gleason T.; Lu Y.; Huang G. D. N. Engl. J. Med. 2018, 378, 507. doi: 10.1056/NEJMoa1507598
[8]	Moy B.; Kirkpatrick P.; Kar S.; Goss P. Nat. Rev. Drug Discovery 2007, 6, 431. doi: 10.1038/nrd2332
[9]	Sordella R.; Bell D. W.; Haber D. A.; Settleman J. Science 2004, 305, 1163. doi: 10.1126/science.1101637
[10]	(a) Sikari R.; Chakraborty G.; Guin A. K.; Paul N. D. J. Org. Chem. 2021, 86, 279. doi: 10.1021/acs.joc.0c02069 pmid: 33314935
	(b) Xu H.-B.; Zhu Y.-Y.; Yang J.-H.; Chai X.-Y.; Dong L. Org. Chem. Front. 2020, 7, 1230. doi: 10.1039/D0QO00084A pmid: 33314935
	(c) Yan Y.; Zhang Y.; Feng C.; Zha Z.; Wang Z. Angew. Chem., Int. Ed. 2012, 51, 8077. doi: 10.1002/anie.v51.32 pmid: 33314935
	(d) Zhang L.; Hu Z.; Dong J.; Zhang X. M.; Xu X. Adv. Synth. Catal. 2018, 360, 1938. doi: 10.1002/adsc.v360.10 pmid: 33314935
	(e) Zhou Z.; Hu K.; Wang J.; Li Z.; Zhang Y.; Zha Z.; Wang Z. ACS Omega 2020, 5, 31963. doi: 10.1021/acsomega.0c04865 pmid: 33314935
[11]	(a) Li C.; An S.; Zhu Y.; Zhang J.; Kang Y.; Liu P.; Wang Y.; Li J. RSC Adv. 2014, 4, 49888. doi: 10.1039/C4RA09240F pmid: 33314935
	(b) Sikari R.; Chakraborty G.; Guin A. K.; Paul N. D. J. Org. Chem. 2021, 86, 279. doi: 10.1021/acs.joc.0c02069 pmid: 33314935
	(c) Chakrabarti K.; Maji M.; Kundu S. Green Chem. 2019, 21, 1999. doi: 10.1039/c8gc03744b pmid: 33314935
	(d) Huo S.; Kong S.; Zeng G.; Feng Q.; Lu G. L. J. Mol. Catal. 2021, 514, 111773. pmid: 33314935
	(e) Kumar G. R. Y.; Begum N. S. New J. Chem. 2021, 45, 9811. doi: 10.1039/D1NJ01115D pmid: 33314935
	(f) Das S.; Mondal R.; Chakraborty G.; Guin A. K.; Das A.; Paul N. D. ACS Catal. 2021, 11, 7498. doi: 10.1021/acscatal.1c00275 pmid: 33314935
	(g) Yamaguchi T.; Sakairi K.; Yamaguchi E.; Tada N.; Itoh A. RSC Adv. 2016, 6, 56892. doi: 10.1039/C6RA04073J pmid: 33314935
[12]	(a) Tan Y.; Jiang W.; Ni P.; Fu Y.; Ding Q. Adv. Synth. Catal. 2022, 364, 3600. doi: 10.1002/adsc.v364.20
	(b) Shariati M.; Imanzadeh G.; Rostami A.; Ghoreishy N.; Kheirjou S. CR Chim. 2019, 22, 337. doi: 10.1016/j.crci.2019.03.003
	(c) Yao S.; Zhou K.; Wang J.; Cao H.; Yu L.; Wu J.; Qiu P.; Xu Q. Green Chem. 2017, 19, 2945. doi: 10.1039/C7GC00977A
	(d) Saha M.; Mukherjee P.; Das A. R. Tetrahedron Lett. 2017, 58, 2044. doi: 10.1016/j.tetlet.2017.04.036
	(e) Liu Q.; Chen H.; Li S.; Guo Y.; Cao S.; Zhao Y. ChemistrySelect 2022, 7, e202201231. doi: 10.1002/slct.v7.22
	(f) Han B.; Wang C.; Han R.-F.; Yu W.; Duan X.-Y.; Fang R.; Yang X.-L. Chem. Commun. 2011, 47, 7818. doi: 10.1039/c1cc12308d
[13]	(a) Gujjarappa R.; Vodnala N.; Reddy V. G.; Malakar C. C. Eur. J. Org. Chem. 2020, 2020, 803. doi: 10.1002/ejoc.v2020.7
	(b) Gujjarappa R.; Maity S. K.; Hazra C. K.; Vodnala N.; Dhiman S.; Kumar A.; Beifuss U.; Malakar C. C. Eur. J. Org. Chem. 2018, 2018, 4628. doi: 10.1002/ejoc.v2018.33
	(c) Ma J.; Wan Y.; Hong C.; Li M.; Hu X.; Mo W.; Hu B.; Sun N.; Jin L.; Shen Z. Eur. J. Org. Chem. 2017, 2017, 3335. doi: 10.1002/ejoc.v2017.23
[14]	Laha J. K.; Panday S.; Tomar M.; Patel K. V. Org. Biomol. Chem. 2021, 19, 845. doi: 10.1039/D0OB00360C
[15]	Yang J.; Xie Z.; Jin L.; Chen X.; Le Z. Org. Biomol. Chem. 2022, 20, 3558. doi: 10.1039/D2OB00219A
[16]	(a) Yuan Y.; Yang J.; Lei A. Chem. Soc. Rev. 2021, 50, 10058. doi: 10.1039/D1CS00150G pmid: 33017147
	(b) Xiong P.; Xu H.-C. Acc. Chem. Res. 2019, 52, 3339. doi: 10.1021/acs.accounts.9b00472 pmid: 33017147
	(c) Jiao K.-J.; Xing Y.-K.; Yang Q. L.; Qiu H.; Mei T.-S. Acc. Chem. Res. 2020, 53, 300. doi: 10.1021/acs.accounts.9b00603 pmid: 33017147
	(d) Shi S.-H.; Liang Y.; Jiao N. Chem. Rev. 2021, 121, 485. doi: 10.1021/acs.chemrev.0c00335 pmid: 33017147
	(e) Minteer S. D.; Baran P. S. Acc. Chem. Res. 2020, 53, 545. doi: 10.1021/acs.accounts.0c00049 pmid: 33017147
	(f) Qian P.; Zha Z.; Wang Z. ChemElectroChem 2020, 7, 2527. doi: 10.1002/celc.v7.12 pmid: 33017147
	(g) Yount J.; Piercey D. G. Chem. Rev. 2022, 122, 8809. doi: 10.1021/acs.chemrev.1c00935 pmid: 33017147
	(h) Cheng X.; Lei A.; Mei T.-S.; Xu H.-C.; Xu K.; Zeng C. CCS Chem. 2022, 4, 1120. doi: 10.31635/ccschem.021.202101451 pmid: 33017147
	(i) Pan Y.; Meng X.; Wang Y.; He M. Chin. J. Org. Chem. 2023, 43, 1416. (in Chinese) doi: 10.6023/cjoc202208004 pmid: 33017147
	( 潘永周, 蒙秀金, 王迎春, 何慕雪, 有机化学, 2023, 43, 1416.) pmid: 33017147
	(j) Zhang H.; Liang S.; Wei D.; Xu K.; Zeng C. Eur. J. Org. Chem. 2022, 2022, e202200794. doi: 10.1002/ejoc.v2022.39 pmid: 33017147
	(k) Wu Y.; Yi H.; Lei A. ACS Catal. 2018, 8, 1192. doi: 10.1021/acscatal.7b04137 pmid: 33017147
	(l) Xiao Q.; Tong Q.-X.; Zhong J.-J. Chin. J. Org. Chem. 2022, 42, 3979. (in Chinese) doi: 10.6023/cjoc202209025 pmid: 33017147
	肖潜, 佟庆笑, 钟建基, 有机化学, 2022, 42, 3979.). doi: 10.6023/cjoc202209025 pmid: 33017147
	(m) Tan Z.; Zhang H.; Xu K.; Zeng C. Sci. China: Chem. 2024, 67, 450. doi: 10.1007/s11430-023-1230-3 pmid: 33017147
	(n) Wei W.; Zhan L.; Gao L.; Huang G.; Ma X. Chin. J. Org. Chem. 2023, 43, 17. (in Chinese) doi: 10.6023/cjoc202205018 pmid: 33017147
	( 魏琬絜, 詹磊, 高雷, 黄国保, 马献力, 有机化学, 2023, 43, 17.) doi: 10.6023/cjoc202205018 pmid: 33017147
[17]	(a) Lin D.-Z.; Huang J.-M. Org. Lett. 2018, 20, 2112. doi: 10.1021/acs.orglett.8b00698
	(b) Lin D.-Z.; Huang J.-M. Org. Lett. 2019, 21, 5862. doi: 10.1021/acs.orglett.9b01971
	(c) Wang H.-B.; Huang J.-M. Adv. Synth. Catal. 2016, 358, 1975. doi: 10.1002/adsc.v358.12
[18]	(a) Wang Q.-Q.; Xu K.; Jiang Y.-Y.; Liu Y.-G.; Sun B.-G.; Zeng C.-C. Org. Lett. 2017, 19, 5517. doi: 10.1021/acs.orglett.7b02589
	(b) Ding H.; Xu K.; Zeng C. C. J. Catal. 2020, 381, 38. doi: 10.1016/j.jcat.2019.10.030
	(c) Li Y.; Liang S.; Wang D.; Xu K.; Zeng C. Synthesis 2023, 55, 3026. doi: 10.1055/a-2147-2863
[19]	Kong X.; Liu Y.; Lin L.; Chen Q.; Xu B. Green Chem. 2019, 21, 3796. doi: 10.1039/C9GC01098J
[20]	Lu F.; Gong F.; Li L.; Zhang K.; Li Z.; Zhang X.; Yin Y.; Wang Y.; Gao Z.; Zhang H.; Lei A. Eur. J. Org. Chem. 2020, 2020, 3257. doi: 10.1002/ejoc.v2020.22
[21]	Zhao F.; Meng N.; Sun T.; Wen J.; Zhao X.; Wei W. Org. Chem. Front. 2021, 8, 6508. doi: 10.1039/D1QO01351C
[22]	(a) Zhao Y.; Meng X.; Cai C.; Wang L.; Gong H. Asian J. Org. Chem. 2022, 11, e202100748. doi: 10.1002/ajoc.v11.4
	(b) Kong X.; Chen Y.; Chen X.; Lu Z.-X.; Wang W.; Ni S.-F.; Cao Z.-Y. Org. Lett. 2022, 24, 2137. doi: 10.1021/acs.orglett.2c00408
	(c) Wang X.; Wu S.; Zhong Y.; Wang Y.; Pan Y.; Tang H. Chin. Chem. Lett. 2023, 34, 107537. doi: 10.1016/j.cclet.2022.05.051
[23]	(a) Wu J.; Shi H.; Liu J.; Wang R.; Zhou J.; Xu X.-L.; Xu H.-J. Org. Chem. Front. 2023, 10, 2459. doi: 10.1039/D3QO00204G
	(b) Dai J.-J.; Teng X.-X.; Fang W.; Xu J.; Xu H.-J. Chin. Chem. Lett. 2022, 33, 1555. doi: 10.1016/j.cclet.2021.09.011
	(c) Zhu X.-X.; Wang H.-Q.; Li C.-G.; Xu X.-L.; Xu J.; Dai J.-J.; Xu H.-J. J. Org. Chem. 2021, 86, 16114. doi: 10.1021/acs.joc.0c02659
[24]	Mangiavacchi1 F.; Mollari1, L.; Bagnoli1, L.; Marini1, F.; Santi1, C. Chem. Heterocycl. Compd. 2018, 54, 478. doi: 10.1007/s10593-018-2292-0

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