A Convenient Approach to Benzosultam-Linked Pyrazole Compounds

doi:10.6023/cjoc202209009

Abstract

Cite this article

Rongchao Lei, Wenjie Lan, Mengzhu Li, Bin Fu. A Convenient Approach to Benzosultam-Linked Pyrazole Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2553-2560.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

References 19

[1]	Takeuchi, Y.; Liu, Z. Heterocycles 2002, 56, 693. doi: 10.3987/REV-01-SR(K)3
[2]	Mao, J.; Baker, D. C. US 6458962, 2003.
[3]	(a) Castro Pineiro, J. L.; Collins, I. J.; Harrison, T. US 20050014369, 2005.
	(b) Supuran, C. T.; Casini, A.; Scozzafava, A. Med. Res. Rev. 2003, 23, 535 doi: 10.1002/(ISSN)1098-1128
[4]	(a) Zhang, H.; Sun, M.-C.; Yin, L.-M.; Wei, D. H.; Song, M.-P.; Yang, D. D.; Niu, J.-L. Org. Chem. Front. 2021, 8, 6888. doi: 10.1039/D1QO01235E pmid: 21894896
	(b) Li, R.-L.; Fang, Q.-Y.; Li, M.-Y.; Wang, X.-S.; Zhao, L.-M. Chem. Commun. 2021, 57, 11322. doi: 10.1039/D1CC04179G pmid: 21894896
	(c) Majumdar, K. C.; Shovan, M. Chem. Rev. 2011, 111, 7749. doi: 10.1021/cr1003776 pmid: 21894896
[5]	(a) Sun, R.; Qiu, Z. X.; Cao, G. R.; Teng, D. W. Tetrahedron 2020, 76, 131201. doi: 10.1016/j.tet.2020.131201 pmid: 23298148
	(b) Nishimura, T.; Noishiki, A.; Tsui, G. C.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 5056. doi: 10.1021/ja300697c pmid: 23298148
	(c) Wang, H.; Jiang, T.; Xu, M.-H. J. Am. Chem. Soc. 2013, 135, 971. doi: 10.1021/ja3110818 pmid: 23298148
	(d) Qiao, B.; Huang, Y.-J.; Nie, J.; Ma, J.-A. Org. Lett. 2015, 17, 4608. doi: 10.1021/acs.orglett.5b02351 pmid: 23298148
	(e) Yu, J.-S.; Zhou, J. Org. Chem. Front. 2016, 3, 298. doi: 10.1039/C5QO00407A pmid: 23298148
[6]	(a) Watanabe, T.; Yuki, S.; Egawa, M.; Nishi, H. J. Pharmacol. Exp. Ther. 1994, 268, 1597. pmid: 9152402
	(b) Kawai, H.; Nakai, H.; Suga, M.; Yuki, S.; Watanabe, T.; Saito, K. I. J. Pharmacol. Exp. Ther. 1997, 281, 921. pmid: 9152402
[7]	Wu, T. W.; Zeng, L. H.; Wu, J.; Fung, K. P. Life Sci. 2002, 71, 2249. doi: 10.1016/S0024-3205(02)01965-3
[8]	Shiohara, H.; Fujikura, H.; Fushimi, N.; Ito, F.; Isaji, M. WO 2002098893, 2002.
[9]	(a) Liu, S.; Bao, X.; Wang, B. Chem. Commun. 2018, 54, 11515. doi: 10.1039/C8CC06196C pmid: 29699396
	(b) Hack, D.; Chauhan, P.; Decker, S. K.; Mizutani, Y.; Raabe, G.; Enders, D. Chem. Commun. 2015, 51, 2266. doi: 10.1039/C4CC09495F pmid: 29699396
	(c) Yetra, S. R.; Mondal, S.; Suresh, E.; Biju, A. Org. Lett. 2015, 17, 1417. doi: 10.1021/acs.orglett.5b00293 pmid: 29699396
	(d) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340. doi: 10.1021/acs.joc.6b00196 pmid: 29699396
	(e) Chauhan, P.; Mahajan, S.; Kaya, U.; Peuronen, A.; Rissanen, K.; Enders, D. J. Org. Chem. 2017, 82, 705. pmid: 29699396
	(f) Maity, R.; Gharui, C.; Sil, A. K.; Pan, S. C. Org. Lett. 2017, 19, 662. doi: 10.1021/acs.orglett.6b03823 pmid: 29699396
	(g) Cheng, C., Zhang, J.; Wang, X.; Miao, Z. J. Org. Chem. 2018, 83, 5450. doi: 10.1021/acs.joc.8b00352 pmid: 29699396
	(h) Vila, C.; Amr, F. I.; Blay, G.; Muňoz, M. C.; Pedro, J. R. Chem.- Asian J. 2016, 11, 1532. doi: 10.1002/asia.201600325 pmid: 29699396
	(i) Rao, K. S.; Ramesh, P.; Trivedi, R.; Kantam, M. L. Tetrahedron Lett. 2016, 57, 1227. doi: 10.1016/j.tetlet.2016.02.008 pmid: 29699396
[10]	(a) Liao, Y. H.; Chen, W. B.; Wu, Z. J.; Du, X. L.; Cun, L. F.; Zhang, X. M.; Yuan, W. C. Adv. Synth. Catal. 2010, 352, 827. doi: 10.1002/adsc.200900764 pmid: 27100356
	(b) Meshram, H. M.; Kumar, N. S.; Nanubolu, J. B.; Rao, L. C.; Rao, N. N. Tetrahedron Lett. 2013, 54, 5941. doi: 10.1016/j.tetlet.2013.08.042 pmid: 27100356
	(c) Li, J. H.; Du, D. M. Org. Biomol. Chem. 2013, 11, 6215. doi: 10.1039/c3ob41045e pmid: 27100356
	(d) Wang, H.; Wang, Y.; Song, H.; Zhou, Z.; Tang, C. Eur. J. Org. Chem. 2013, 2013, 4844. doi: 10.1002/ejoc.201300460 pmid: 27100356
	(e) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340. doi: 10.1021/acs.joc.6b00196 pmid: 27100356
	(f) Hack, D.; Dürr, A. B.; Deckers, K.; Chauhan, P.; Seling, N.; Rübenach, L.; Mertens, L.; Raabe, G.; Schoenebeck, F.; Enders, D. Angew. Chem.,Int. Ed. 2016, 55, 1797. doi: 10.1002/anie.201510602 pmid: 27100356
	(g) Rana, N. K.; Jha, R. K.; Joshi, H.; Singh, V. K. Tetrahedron Lett. 2017, 58, 2135. doi: 10.1016/j.tetlet.2017.04.059 pmid: 27100356
	(h) Xu, Y.; Sun, P.; Song, Q.; Lai, X.; Liu, W.; Xia, T.; Huang, Y. Y.; Shen, Y. Eur. J. Org. Chem. 2017, 2017, 2998. pmid: 27100356
[11]	(a) Gogoi, S.; Zhao, C. G.; Ding, D. Org. Lett. 2009, 11, 2249. doi: 10.1021/ol900538q pmid: 26942717
	(b) Alba, A. N.; Zea, A.; Valero, G.; Calbet, T.; Font-Bardía, M.; Mazzanti, A.; Moyano, A.; Rios, R. Eur. J. Org. Chem. 2011, 2011, 1318. doi: 10.1002/ejoc.v2011.7 pmid: 26942717
	(c) Enders, D.; Grossmann, A.; Gieraths, B.; Düzdemir, M.; Merkens, C. Org. Lett. 2012, 14, 4254. doi: 10.1021/ol301983f pmid: 26942717
	(d) Li, J. H.; Du, D. M. RSC Adv. 2014, 4, 14538. doi: 10.1039/c3ra45974h pmid: 26942717
	(e) Yetra, S. R.; Mondal, S.; Suresh, E.; Biju, A. T. Org. Lett. 2015, 17, 1417. doi: 10.1021/acs.orglett.5b00293 pmid: 26942717
	(f) Kumarswamyreddy, N.; Kesavan, V. Org. Lett. 2016, 18, 1354. doi: 10.1021/acs.orglett.6b00287 pmid: 26942717
[12]	Mazzanti, A.; Calbet, T.; Font-Bardia, M.; Moyano, A.; Rios, R. Org. Biomol. Chem. 2012, 10, 1645. doi: 10.1039/c2ob06553c pmid: 22237869
[13]	(a) Gogoi, S.; Zhao, C. G. Tetrahedron Lett. 2009, 50, 2252. doi: 10.1016/j.tetlet.2009.02.210
	(b) Xie, J.; Xing, X. Y.; Sha, F.; Wu, Z. Y.; Wu, X. Y. Org. Biomol. Chem. 2016, 14, 8346. doi: 10.1039/C6OB01256F
[14]	(a) Keyume, A.; Esmayil, Z.; Wang, L. J.; Jun, F. Tetrahedron 2014, 70, 3976. doi: 10.1016/j.tet.2014.04.088
	(b) Fan, W.-T.; Yang, X.-P.; Yang, H.-P.; Lv, H.-P.; Wang, X.-W.; Wang, Z. Org. Lett. 2020, 22, 3936. doi: 10.1021/acs.orglett.0c01221
	(c) Bao, X. Z.; Wei, S.-Q.; Qu, J.-P.; Wang, B. M. Chem. Commun. 2018, 54, 2028. doi: 10.1039/C8CC00154E
	(d) Li, L.; Liu, Z.-T.; Hu, X.-P. Chem. Commun. 2018, 54, 12033. doi: 10.1039/C8CC05706K
	(e) Ni, C. J.; Tong, X. F. J. Am. Chem. Soc. 2016, 138, 7872. doi: 10.1021/jacs.6b04935
[15]	(a) Feng, J.; Ablajan, K.; Sali, A. Tetrahedron 2014, 70, 484. doi: 10.1016/j.tet.2013.11.019
	(b) Tan, C.-Y.; Lu, H.; Zhang, J.-L.; Liu, J.-Y.; Xu, P.-F. J. Org. Chem. 2020, 85, 594. doi: 10.1021/acs.joc.9b02684
	(c) Xu, Y.-W.; Li, L.; Hu, X.-P. Org. Lett. 2020, 22, 9534. doi: 10.1021/acs.orglett.0c03587
	(d) Tang, C.-K.; Zhou, Z.-Y.; Xia, A.-B.; Bai, L.; Liu, J.; Xu, D.-Q.; Xu, Z.-Y. Org. Lett. 2018, 20, 5840. doi: 10.1021/acs.orglett.8b02525
	(e) Kale, S. B.; Jori, P. K.; Thatikonda, T.; Gonnade, R. G.; Das, U. Org. Lett. 2019, 21, 7736. doi: 10.1021/acs.orglett.9b02641
	(f) Hack, D.; Dürr, A. B.; Deckers, K.; Chauhan, P.; Seling, N.; Rüenach, L.; Mertens, L.; Raabe, G.; Schoenebeck, F.; Enders, D. Angew. Chem., nt. Ed. 2016, 55, 1797.
[16]	(a) Lan, W. J.; Lei, R. C.; Luo, J. Y.; Qin, Z. H.; Fu, B.; Xie, L. ChemistrySelect 2022, 7, 3670.
	(b) Xie, L.; Ma, H.-L; Li, J.-Q.; Yu, X.; Qin, Z. H.; Fu, B. Org. Chem. Front. 2017, 4, 1858. doi: 10.1039/C7QO00370F
[17]	(a) Li, S.-W.; Wan, Q.; Kang, Q. Org. Lett. 2018, 20, 1312. doi: 10.1021/acs.orglett.8b00040 pmid: 31657819
	(b) Sharma, A.; Sharma, V.; Chimni, S. S. Org. Biomol. Chem. 2019, 17, 9514. doi: 10.1039/c9ob01700c pmid: 31657819
[18]	Yan, Z.; Wu, B.; Gao, X.; Chen, M. W.; Zhou, Y. G. Org. Lett. 2016, 18, 692. doi: 10.1021/acs.orglett.5b03664
[19]	(a) Branä, M. F.; Gradillas, A.; Ovalles, A. G.; Lopez, B.; Acero, N.; Llinares, F.; Mingarro, D. M. Bioorg. Med. Chem. 2006, 14, 9. doi: 10.1016/j.bmc.2005.09.059
	(b) Wang, X.-j.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713.

Entry	Solvent	Base	T/℃	Yield/%
1	CHCl₃	Et₃N	r.t.	52
2	CH₂Cl₂	Et₃N	r.t.	48
3	Et₂O	Et₃N	r.t.	65
4	CH₃CO₂Et	Et₃N	r.t.	41
5	Toluene	Et₃N	r.t.	44
6	THF	Et₃N	r.t.	98
7	THF	Na₂CO₃	r.t.	60
8	THF	K₂CO₃	r.t.	40
9	THF	Cs₂CO₃	r.t.	41
10	THF	NaOH	r.t.	30
11	THF	MeONa	r.t.	30
12	THF	Pyridine	r.t.	62
13	THF	DIEPA	r.t.	75
14	THF	Et₃N	0	93
15	THF	Et₃N	35	83

Entry	Solvent	Base	T/℃	Yield/%
1	CHCl₃	Et₃N	r.t.	52
2	CH₂Cl₂	Et₃N	r.t.	48
3	Et₂O	Et₃N	r.t.	65
4	CH₃CO₂Et	Et₃N	r.t.	41
5	Toluene	Et₃N	r.t.	44
6	THF	Et₃N	r.t.	98
7	THF	Na₂CO₃	r.t.	60
8	THF	K₂CO₃	r.t.	40
9	THF	Cs₂CO₃	r.t.	41
10	THF	NaOH	r.t.	30
11	THF	MeONa	r.t.	30
12	THF	Pyridine	r.t.	62
13	THF	DIEPA	r.t.	75
14	THF	Et₃N	0	93
15	THF	Et₃N	35	83

Entry	R²	R³	Product	Yield/%
1	2-MeC₆H₄	Ph	3ab	94
2	2-CF₃C₆H₄	Ph	3ac	85
3	3-MeC₆H₄	Ph	3ad	82
4	3-FC₆H₄	Ph	3ae	98
5	4-MeOC₆H₄	Ph	3af	96
6	4-BrC₆H₄	Ph	3ag	91
7	Naphthyl	Ph	3ah	87
8	Ph	4-MeC₆H₄	3ai	98
9	Ph	4-ClC₆H₄	3aj	87
10	Ph	3-MeOC₆H₄	3ak	82
11	Ph	3-BrC₆H₄	3al	82
12	Ph	2-FC₆H₄	3am	92
13	Ph	Cyclohexyl	3an	90
14	Ph	H	3ao	—

Entry	R²	R³	Product	Yield/%
1	2-MeC₆H₄	Ph	3ab	94
2	2-CF₃C₆H₄	Ph	3ac	85
3	3-MeC₆H₄	Ph	3ad	82
4	3-FC₆H₄	Ph	3ae	98
5	4-MeOC₆H₄	Ph	3af	96
6	4-BrC₆H₄	Ph	3ag	91
7	Naphthyl	Ph	3ah	87
8	Ph	4-MeC₆H₄	3ai	98
9	Ph	4-ClC₆H₄	3aj	87
10	Ph	3-MeOC₆H₄	3ak	82
11	Ph	3-BrC₆H₄	3al	82
12	Ph	2-FC₆H₄	3am	92
13	Ph	Cyclohexyl	3an	90
14	Ph	H	3ao	—

苯并磺内酰胺联吡唑化合物的简便合成

A Convenient Approach to Benzosultam-Linked Pyrazole Compounds

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 19

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[2]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[3]	Yang Sun, Yang Wang, Zichan Zhang, Ye Qian, Guicheng Luo, Beibei Zhou, Lisha Miao, Yudie Chen, Hong Dai, Baolin Xu, Zhengguang Wu. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1584-1590.
[4]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[5]	Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang, Jijiang Wang. Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1843-1848.
[6]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[7]	Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.
[8]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[9]	Yunshu Liu, Guodong Zhao, Wenju Wu, Yunze Wang, Yanchao Yu, Jun You, Bo Liu. Study on Asymmetric Conjugate Cyanation of 3,5-Dimethyl-N-α,β-unsaturated Acylpyrazole Catalyzed by Magnesium-Bisoxazoline Complex [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 208-217.
[10]	Haojie Ma, Xiaoqiang Zhou, Bo Han, Ran Li, Xueyan Hou, Xingyue Ji, Yuqi Zhang, Guosheng Huang, Jijiang Wang. A Catalyst-Free One-Pot Protocol for the Construction of Substituted Sulfonyl Pyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3710-3716.
[11]	Jiaoli Ma, Penghu Guo, Jing Li, Xincheng Liao, Huicheng Cheng. Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3214-3222.
[12]	Wenqing Zhu, Tingyi Xu, Wenyong Han. Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1275-1287.
[13]	Guanglei Li, Haifeng Huang, Jun Yang, Hongzhen Duan. Progress in the Synthesis of Energetic Salts Based on Pyrazole [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1466-1488.
[14]	Haojie Ma, Zhou Sun, Jinlei Liu, Xia Zhang, Huali Cui, Yuqi Zhang, Jijiang Wang. CBr₄-Mediated Intermolecular Cyclization Reaction: Efficient Synthesis of Substituted N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4353-4360.
[15]	Min Zhao, Fei Li, Yizheng Cheng, Youming Wang, Zhenghong Zhou. Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4039-4049.