Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp3 C—H Bonds

doi:10.6023/cjoc202203030

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2449-2455.DOI: 10.6023/cjoc202203030 Previous Articles Next Articles

ARTICLES

碘化铵催化sp³ C—H双胺化反应合成喹唑啉-4(3H)-酮

喻晓哓, 柏汪恒, 朱建业, 张雨婷, 张梦茹, 吴际伟^*()

安徽科技学院化学与材料工程学院安徽凤阳 233100

收稿日期:2022-03-16 修回日期:2022-04-25 发布日期:2022-05-26
通讯作者: 吴际伟
基金资助:
安徽省自然科学基金(2008085QB66); 安徽科技学人才引进(HCYJ201903); 安徽省大学生创新创业训练计划(S202010879140)

Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds

Xiaoxiao Yu, Wangheng Bai, Jianye Zhu, Yuting Zhang, Mengru Zhang, Jiwei Wu()

College of Chemistry and Materials Engineering, Anhui Science and Technology University, Fengyang, Anhui 233100

Received:2022-03-16 Revised:2022-04-25 Published:2022-05-26
Contact: Jiwei Wu
Supported by:
Natural Science Foundation of Anhui Province(2008085QB66); Anhui Science and Technology Talent Introduction Project(HCYJ201903); Innovation and Entrepreneurship Training Program for College Students in Anhui Province(S202010879140)

1. .pdf(1390KB)

Abstract

A novel method for synthesizing quinazoline-4(3H)-ones was developed by using inexpensive ammonium iodide as catalyst via dual amination of aromatic benzylic position sp³ C—H bonds. In this reaction, ammonium iodide was used as catalyst, tert-butanol hydrogen peroxide (TBHP) was used as oxidant and dimethyl sulfoxide (DMSO) was used as solvent. The reaction was carried out at 100 ℃ for 20 h to obtain quinazoline-4(3H)-ones compounds with moderate to excellent yields. Furthermore, the mechanism investigations were conducted, and the possible reaction mechanism was depicted. Due to the method does not require use metal catalyst, and has the advantages of simple conditions and wide substrate application range, the present protocol has the potential to be widely applied.

Key words: ammonium iodine catalysis, quinazolin-4(3H)-ones, dual amination of sp³C—H bonds

Cite this article

Xiaoxiao Yu, Wangheng Bai, Jianye Zhu, Yuting Zhang, Mengru Zhang, Jiwei Wu. Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2449-2455.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 20

[1]	(a) Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7, 659. doi: 10.2174/1385272033486738
	(b) Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787. doi: 10.1016/j.tet.2006.07.098
[2]	(a) Cao, S. L.; Feng, Y. P.; Jiang, Y. Y.; Liu, S.; Ding, Y. G.; Li, R. T. Bioorg. Med. Chem. Lett. 2005, 15, 1915. doi: 10.1016/j.bmcl.2005.01.083
	(b) He, L.; Li, H.; Chen, J.; Wu, X.-F. RSC Adv. 2014, 4, 12065. doi: 10.1039/C4RA00351A
[3]	(a) De Laszlo, S. E.; Quagliato, C. S.; Greenlee, W. J.; Patchett, A. A.; Lotti, V. J.; Chen, T. B.; Scheck, S. A.; Faust, A. J. Med. Chem. 1993, 36, 3207. pmid: 10579832
	(b) Kung, P. P.; Casper, M. D.; Cook, K. L.; Wilson-Lingardo, L.; Risen, L. M.; Vickers, T.; Ranken, A. R.; Blyn, L. B.; Wyatt, J. R.; Cook, P. D. J. Med. Chem. 1999, 42, 4705. pmid: 10579832
	(c) Connolly, D. J.; Cusack, D.; O’Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153. doi: 10.1016/j.tet.2005.07.010 pmid: 10579832
[4]	(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. doi: 10.1021/cr020033s
	(b) Dong, Y.; Zhang, J.; Yang, J.; Yan, C.; Wu, Y. New J. Chem. 2021, 45, 15344. doi: 10.1039/D1NJ03179A
	(c) Philips, A.; Raja, D.; Arumugam, A.; Lin, W.-Y.; Chandru Senadi, G. Asian J. Org. Chem. 2021, 10, 1795. doi: 10.1002/ajoc.202100317
	(d) Bao, Y.; Yan, Y.; Xu, K.; Su, J.; Zha, Z.; Wang, Z. J. Org. Chem. 2015, 80, 4736. doi: 10.1021/acs.joc.5b00191
[5]	(a) Purandare, A. V.; Gao, A. M.; Wan, H. H.; Somerville, J.; Burke, C.; Seachord, C.; Vaccaro, W.; Wityak, J.; Poss, M. A. Bioorg. Med. Chem. Lett. 2005, 15, 2669. pmid: 15863339
	(b) Potewar, T. M.; Nadaf, R. N.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Synth. Commun. 2005, 35, 231. doi: 10.1081/SCC-200048433 pmid: 15863339
[6]	(a) Hisano, T.; Ichikawa, M.; Nakagawa, A.; Tsuji, M. Chem. Pharm. Bull. 1975, 23, 1910. doi: 10.1248/cpb.23.1910 pmid: 20800934
	(b) Mitobe, Y.; Ito, S.; Mizutani, T.; Nagase, T.; Sato, N.; Tokita, S. Bioorg. Med. Chem. Lett. 2009, 19, 4075. doi: 10.1016/j.bmcl.2009.06.025 pmid: 20800934
	(c) Balakumar, C.; Lamba, P.; Kishore, D. P.; Narayana, B. L.; Rao, K. V.; Rajwinder, K.; Rao, A. R.; Shireesha, B.; Narsaiah, B. Eur. J. Med. Chem. 2010, 45, 4904. doi: 10.1016/j.ejmech.2010.07.063 pmid: 20800934
[7]	Hikawa, H.; Ino, Y.; Suzuki, H.; Yokoyama, Y. J. Org. Chem. 2012, 77, 7046. doi: 10.1021/jo301282n
[8]	Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. Org. Biomol. Chem. 2012, 10, 240. doi: 10.1039/C1OB06516E
[9]	(a) Zhou, J.; Fang, J. J. Org. Chem. 2011, 76, 7730. doi: 10.1021/jo201054k
	(b) Zhao, D.; Zhou, Y.-R.; Shen, Q.; Li, J.-X. RSC Adv. 2014, 4, 6486. doi: 10.1039/c3ra46363j
[10]	Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F. RSC Adv. 2014, 4, 8. doi: 10.1039/C3RA45765F
[11]	Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Green Chem. 2013, 15, 2713. doi: 10.1039/c3gc41186a
[12]	Wei, H.; Li, T.; Zhou, Y.; Zhou, L.; Zeng, Q. Synthesis 2013, 3349.
[13]	(a) Wu, X.-F.; He, L.; Neumann, H.; Beller, M. Chem. Eur. J. 2013, 19, 12635. doi: 10.1002/chem.201302182 pmid: 24810598
	(b) Li, H.; He, L.; Neumann, H.; Beller, M.; Wu, X. F. Green Chem. 2014, 16, 1336. doi: 10.1039/C3GC42089B pmid: 24810598
	(c) Jiang, X.; Tang, T.; Wang, J.-M.; Chen, Z.; Zhu, Y.-M.; Ji, S.-J. J. Org. Chem. 2014, 79, 5082. doi: 10.1021/jo500636y pmid: 24810598
	(d) You, S.; Huang, B.; Yan, T.; Cai, M. J. Organomet. Chem. 2018, 875, 35. doi: 10.1016/j.jorganchem.2018.09.003 pmid: 24810598
	(e) Ram, S.; Sharma, A. K.; Das, P. Chem. Eur. J. 2019, 25, 14506. doi: 10.1002/chem.201902776 pmid: 24810598
[14]	(a) Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048. doi: 10.1021/ja0647351
	(b) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780. doi: 10.1021/cr100379j
	(c) Tang, S.; Wang, P.; Li, H.; Lei, A. Nat. Commun. 2016, 7, 11676. doi: 10.1038/ncomms11676
	(d) Hu, X.; Zhang, G.; Bu, F.; Lei, A. Angew. Chem. Int. Ed. 2018, 57, 1286. doi: 10.1002/anie.201711359
	(e) Liu, Y.; Shi, B.; Liu, Z.; Gao, R.; Huang, C.; Alhumade, H.; Wang, S.; Qi, X.; Lei, A. J. Am. Chem. Soc. 2021, 143, 20863. doi: 10.1021/jacs.1c09341
[15]	Zhao, D.; Wang, T.; Li, J. Chem. Commun. 2014, 50, 6471. doi: 10.1039/C4CC02648A
[16]	Li, Q.; Huang, Y.; Chen, T.; Zhou, Y.; Xu, Q.; Yin, S.; Han, L. Org. Lett. 2014, 16, 3672. doi: 10.1021/ol501454j
[17]	(a) Yang, L.; Shi, X.; Hu, B.; Wang, L. Asian J. Org. Chem. 2016, 5, 494. doi: 10.1002/ajoc.201600041
	(b) Liu, H.; Zhai, T.; Ding, S.; Hou, Y.; Zhang, X.; Feng, L.; Ma, C. Org. Chem. Front. 2016, 3, 1096. doi: 10.1039/C6QO00231E
[18]	Jang, Y.; Lee, S. B.; Hong, J.; Chun, S.; Lee, J.; Hong, S. Org. Biomol. Chem. 2020, 18, 5435. doi: 10.1039/D0OB00866D
[19]	(a) Tan, C.; Liu, Y.; Liu, X.; Jia, H.; Xu, K.; Huang, S.; Wang, J.; Tan, J. Org. Chem. Front. 2020, 7, 780. doi: 10.1039/C9QO01489F
	(b) Tan, C.; Liu, X.; Jia, H.; Zhao, X.; Chen, J.; Wang, Z.; Tan, J. Chem. Eur. J. 2020, 26, 881. doi: 10.1002/chem.201904237
[20]	(a) Zhao, D.; Shen, Q.; Lia, J.-X. Adv. Synth. Catal. 2015, 357, 339. doi: 10.1002/adsc.201400827
	(b) Aruri, H.; Singh, U.; Kumar, S.; Kushwaha, M.; Gupta, A. P.; Wakarma, R. A. V.; Singh, P. P. Org. Lett. 2016, 18, 3638. doi: 10.1021/acs.orglett.6b01684

碘化铵催化sp³ C—H双胺化反应合成喹唑啉-4(3H)-酮

Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 20

Related Articles 0

Recommended Articles

Metrics

Comments

Entry	Cat.	[O]	Solvent	Time/h	Yield^b/%
1	TBAI	TBHP	DMSO	20	77
2	KI	TBHP	DMSO	20	76
3	I₂	TBHP	DMSO	20	78
4	NH₄I	TBHP	DMSO	20	90
5	ZnI₂	TBHP	DMSO	20	83
6	NIS	TBHP	DMSO	20	36
7	—	TBHP	DMSO	20	0
8	NH₄Cl	TBHP	DMSO	20	0
9	NH₄I	TBHP	PhCl	20	47
10	NH₄I	TBHP	PhCH₃	20	36
11	NH₄I	TBHP	DMF	20	29
12	NH₄I	TBPB	DMSO	20	63
13	NH₄I	DTBP	DMSO	20	71
14	NH₄I	H₂O₂	DMSO	20	0
15	NH₄I	Na₂S₂O₈	DMSO	20	0
16	NH₄I	(NH₄)₂S₂O₈	DMSO	20	0
17	NH₄I	—	DMSO	20	0
18	NH₄I	TBHP	DMSO	12	53
19	NH₄I	TBHP	DMSO	16	74
20	NH₄I	TBHP	DMSO	24	90
21^c	NH₄I	TBHP	DMSO	20	63
22^d	NH₄I	TBHP	DMSO	20	87
23^e	NH₄I	TBHP	DMSO	20	76
24^f	NH₄I	TBHP	DMSO	20	90

碘化铵催化sp3 C—H双胺化反应合成喹唑啉-4(3H)-酮