Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions

doi:10.6023/cjoc202304002

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3977-3988.DOI: 10.6023/cjoc202304002 Previous Articles Next Articles

磁性纳米负载对甲苯磺酸催化串联合成稠合多环的1,5-苯并氧氮杂䓬类化合物

李硕, 王明亮, 周来运, 王兰芝^*()

河北师范大学化学与材料科学学院河北省有机功能分子重点实验室石家庄 050024

收稿日期:2023-04-04 修回日期:2023-05-29 发布日期:2023-06-26
基金资助:
国家自然科学基金(21776060)

Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions

Shuo Li, Mingliang Wang, Laiyun Zhou, Lanzhi Wang()

Key Laboratory of Organic Functional Molecules of Hebei Province, College of Chemistry & Materials Science, Hebei Normal University, Shijiazhuang 050024

Received:2023-04-04 Revised:2023-05-29 Published:2023-06-26
Contact: * E-mail: wanglanzhi@126.com
Supported by:
National Natural Science Foundation of China(21776060)

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Abstract

1,5-Benzoxazepine is an important active substance found in the development of new drugs. It has the properties of anticonvulsant, anti-tumor and improving cerebral ischemia. In this work, novel, efficient and green three-component domino reactions were developed, which used substituted o-aminophenol, β-cyclic diketones and active carbonyl compounds as raw materials, self-made magnetic nano-supported p-toluenesulfonic acid (CoFe₂O₄@SiO₂-PTSA) as catalyst, anhydrous ethanol as solvent, at room temperature. 37 fused 1,5-benzoxazepines with diverse structures were synthesized in one pot, and the mechanism of catalytic domino synthesis was proposed. This method abandons the traditional strong base dehalogenation hydrogen coupling method of aromatic halides, and has the advantages of novel synthesis method, mild reaction conditions, green reaction process, high efficiency, short time, and recyclable magnetic nanocatalyst, which provides a methodological reference for the effective synthesis of such compounds.

Key words: 1,5-benzoxazepine, multicomponent domino reaction, green synthesis

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Shuo Li, Mingliang Wang, Laiyun Zhou, Lanzhi Wang. Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3977-3988.

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References 24

[1]	Ma, T.; Li, X.; Ping, Y. Y.; Kong, W. Q. Chin. J. Chem. 2022, 40, 2212. doi: 10.1002/cjoc.v40.18
[2]	Zhu, X. Y.; Ran, C. K.; Wen, M.; Guo, G. L.; Liu, Y.; Liao, L. L.; Li, Y. Z.; Li, M. L.; Yu, D. G. Chin. J. Chem. 2021, 39, 3231. doi: 10.1002/cjoc.v39.12
[3]	Wang, L. Z.; Hua, Z. X.; Niu, W. G. Chin. J. Org. Chem. 2010, 30, 1664. (in Chinese)
	(王兰芝, 花中霞, 牛文刚, 有机化学, 2010, 30, 1664.)
[4]	Meng, J.; Ding, X.; Yu, X.; Deng, W. P. Tetrahedron 2016, 72, 176. doi: 10.1016/j.tet.2015.11.021
[5]	Hossein, Y.; Heshmatoallah, A.; Mahmood, T. Res. Chem. Intermed. 2016, 43, 3283. doi: 10.1007/s11164-016-2825-z
[6]	Vessally, E.; Hosseinzadeh-Khanmiri, R.; Babazadeh, M.; Ghorbani-Kalhor, E.; Edjlali, L. Appl. Organomet. Chem. 2017, 31, e3603. doi: 10.1002/aoc.v31.5
[7]	Yao, C.; Bao, Y.; Lu, T.; Zhou, Q. F. Org. Lett. 2018, 20, 2152. doi: 10.1021/acs.orglett.8b00382
[8]	Narasingam, M.; Vijeepallam, K.; Mohamed, Z.; Pandy, V. Biomed Pharmacother 2017, 96, 944. doi: S0753-3322(17)35029-1 pmid: 29217165
[9]	Arora, N.; Dhiman, P.; Kumar, S.; Singh, G.; Monga, V. Bioorg. Chem. 2020, 97, 103668. doi: 10.1016/j.bioorg.2020.103668
[10]	Thiyagamurthy, P.; Khan, F. R. N. ChemistrySelect 2020, 5, 2610. doi: 10.1002/slct.v5.8
[11]	Greene, L. M.; Butini, S.; Campiani, G.; Williams, D. C.; Zisterer, D. M. J. Cancer 2016, 7, 2367. pmid: 27994676
[12]	Fiore, D.; Proto, M. C.; Pisanti, S.; Picardi, P.; Zottola, A. C. P.; Butini, S.; Gemma, S.; Casagni, A.; Laezza, C.; Vitale, M.; Ligresti, A.; Marzo, V. D.; Zisterer, D. M.; Nathwani, S.; Williams, D. C.; Campiani, G.; Gazzerro, P.; Bifulco, M. Cancer Biol. Ther. 2016, 17, 849.
[13]	Barve, I. J.; Thikekar, T. U.; Sun, C. M. Org. Lett. 2017, 19, 2370. doi: 10.1021/acs.orglett.7b00907
[14]	Sun, X.; Guo, X. Q.; Chen, L. M.; Kang, T. R. Chem.-Eur. J. 2021, 27, 4312 doi: 10.1002/chem.202005124 pmid: 33326645
[15]	Ghandi, M.; Zarezadeh, N.; Abbasi, A. Mol. Diversity 2016, 20, 483. doi: 10.1007/s11030-015-9651-x
[16]	Guo, S. G.; Zhong, X. R.; Gong, B. W.; Cui, H. M.; Xiang, J. B. Chem. Heterocycl. Compd. 2016, 52, 326. doi: 10.1007/s10593-016-1883-x
[17]	Li, B. L.; Zhang, M.; Hu, H. C.; Du, X.; Zhang, Z. H. New J. Chem. 2014, 38, 2435. doi: 10.1039/c3nj01368e
[18]	Zhang, M.; Liu, P.; Liu, Y. H.; Shang, Z. R.; Hu, H. C.; Zhang, Z. H. RSC Adv. 2016, 6, 106160. doi: 10.1039/C6RA19579B
[19]	Sun, Y. W.; Zhou, L. Y.; Wang, L. Z. Chin. J. Org. Chem. 2019, 39, 3516. (in Chinese) doi: 10.6023/cjoc201904026
	(孙悦玮, 周来运, 王兰芝, 有机化学, 2019, 39, 3516.) doi: 10.6023/cjoc201904026
[20]	Wang, M. L.; Yin, L. Y.; Wen, T. T.; Zhang, X.; Gao, J.; Wang, L. Z. Chin. J. Org. Chem. 2022, 42, 160. (in Chinese) doi: 10.6023/cjoc202106028
	(王明亮, 尹刘燕, 温甜甜, 张晓, 高杰, 王兰芝, 有机化学, 2022, 42, 160.) doi: 10.6023/cjoc202106028
[21]	Wang, Z. Y.; Zhao, B. L.; Liu, Y. Y.; Wan, J. P. Adv. Synth. Catal. 2022, 364, 1508. doi: 10.1002/adsc.v364.9
[22]	Guo, Y. H.; Liu, Y. Y; Wan, J. P. Chin. Chem. Lett. 2022, 33, 855. doi: 10.1016/j.cclet.2021.08.003
[23]	Wu, W. P.; Wu, X, Fan, S. X.; Zhu, J. Org. Lett. 2022, 24, 7850. doi: 10.1021/acs.orglett.2c03288
[24]	Yu, Q.; Liu, Y. Y.; Wan, J. P. Chin. Chem. Lett. 2021, 32, 3514. doi: 10.1016/j.cclet.2021.04.037

Entry	Solvent	Temp./℃	Catalyst^b	Time/h	Yield^d/%
1	EtOH	r.t.^d	—	14.0	—
2	EtOH	r.t.	CeCl₃	12.0	23
3	EtOH	r.t.	CoCl₂	12.0	26
4	EtOH	r.t.	PTA(磷钨酸)	6.5	34
5	EtOH	r.t.	PMA(磷钼酸)	6.5	33
6	EtOH	r.t.	AcOH(乙酸)	6.0	67
7	EtOH	r.t.	PTSA(对甲苯磺酸)	6.0	73
8	EtOH	r.t.	CoFe₂O₄	12.0	25
9	EtOH	r.t.	CoFe₂O₄@SiO₂-PTSA^e	7.0	80
10	EtOH	0	CoFe₂O₄@SiO₂-PTSA	10.0	47
11	EtOH	50	CoFe₂O₄@SiO₂-PTSA	6.0	55
12	EtOH	75	CoFe₂O₄@SiO₂-PTSA	6.0	49
13	MeOH	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	78
14	PhMe	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	37
15	MeCN	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	41
16	DCE	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	46
17	DCM	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	42
18	THF	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	25

Entry	Solvent	Temp./℃	Catalyst^b	Time/h	Yield^d/%
1	EtOH	r.t.^d	—	14.0	—
2	EtOH	r.t.	CeCl₃	12.0	23
3	EtOH	r.t.	CoCl₂	12.0	26
4	EtOH	r.t.	PTA(磷钨酸)	6.5	34
5	EtOH	r.t.	PMA(磷钼酸)	6.5	33
6	EtOH	r.t.	AcOH(乙酸)	6.0	67
7	EtOH	r.t.	PTSA(对甲苯磺酸)	6.0	73
8	EtOH	r.t.	CoFe₂O₄	12.0	25
9	EtOH	r.t.	CoFe₂O₄@SiO₂-PTSA^e	7.0	80
10	EtOH	0	CoFe₂O₄@SiO₂-PTSA	10.0	47
11	EtOH	50	CoFe₂O₄@SiO₂-PTSA	6.0	55
12	EtOH	75	CoFe₂O₄@SiO₂-PTSA	6.0	49
13	MeOH	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	78
14	PhMe	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	37
15	MeCN	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	41
16	DCE	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	46
17	DCM	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	42
18	THF	r.t.	CoFe₂O₄@SiO₂-PTSA	7.0	25

磁性纳米负载对甲苯磺酸催化串联合成稠合多环的1,5-苯并氧氮杂䓬类化合物

Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions

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