Selenium Mediated Cyclization Reaction of Isonitriles with o-Aminophenols to Synthesize 2-Aminobenzoxazoles

doi:10.6023/cjoc202407001

Abstract

Selenium mediated cyclization reaction of isonitriles with o-aminophenols leading to 2-aminobenzoxazoles has been reported. The present method, which simply utilizes element selenium as promoter and ^tBuONa as base, provides a green and efficient approach to synthesize various 2-aminobenzoxazoles under mild conditions. This reaction has the advantages of simple operation and metal-free condition. 2-Aminobenzothiazole and 2-aminobenzimidazole could also be synthesized through this methodology.

Key words: metal-free, selenium, isonitriles, o-aminophenols, 2-aminobenzoxazoles

Cite this article

Zheng Wang, Yuqin Lan, Zhiyi Zhou, Yingzi Tan, Zongcheng Wang. Selenium Mediated Cyclization Reaction of Isonitriles with o-Aminophenols to Synthesize 2-Aminobenzoxazoles[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1379-1385.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 21

[1]	(a) Alper-Hayta, S.; Arisoy, M.; Temiz-Arpaci, Ö.; Yildiz, I.; Aki, E.; Özkan, S.; Kaynak, F. Eur. J. Med. Chem. 2008, 43, 2568. doi: 10.1016/j.ejmech.2007.12.019 pmid: 1560442
	(b) Safak, C.; Erdogan, H.; Palaska, E.; Sunal, R.; Duru, S. J. Med. Chem. 1992, 35, 1296. pmid: 1560442
	(c) Feng, M. H.; Tang, B. Q.; Liang, S. H.; Jiang, X. F. Curr. Top. Med. Chem. 2016, 16, 1200. pmid: 1560442
	(d) Hal, I. H.; Peaty, N. J.; Henry, J. R.; Easmon, J.; Heinisch, G.; Pürstinger, G. Arch. Pharm. 1999, 332, 115. pmid: 1560442
	(e) Hou, J.-C.; Ji, H.-T.; Lu, Y.-H.; Wang, J.-S.; Xu, Y.-D.; Zeng, Y.-Y.; He, W.-M. Chin. Chem. Lett. 2024, 35, 109514. pmid: 1560442
	(f) Chen, X.; Ouyang, W.-T.; Li, X.; He, W.-M. Chin. J. Org. Chem. 2023, 43, 4213 (in Chinese). pmid: 1560442
	(陈祥, 欧阳文韬, 李潇, 何卫民, 有机化学, 2023, 43, 4213.) doi: 10.6023/cjoc202307026 pmid: 1560442
[2]	(a) Pochetti, G.; Mitro, N.; Lavecchia, A.; Gilardi, F.; Besker, N.; Scotti, E.; Aschi, M.; Re, N.; Fracchiolla, G.; Laghezza, A.; Tortorella, P.; Montanari, R.; Novellino, E.; Mazza, F.; Crestani, M.; Loiodice, F. J. Med. Chem. 2010, 53, 4354. doi: 10.1021/jm9013899 pmid: 20462215
	(b) Kohler, P. C.; Ritschel, T.; Schweizer, W. B.; Klebe, G.; Diederich, F. Chem.-Eur. J. 2009, 15, 10809. pmid: 20462215
[3]	Chai, J.-Y.; Jung, B.-K.; Hong, S.-J. Korean J. Parasitol. 2021, 59, 189.
[4]	Liu, K. G.; Lo, J. R.; Comery, T. A.; Zhang, G. M.; Zhang, J. Y.; Kowal, D. M.; Smith, D. L.; Di, L.; Kerns, E. H.; Schechter, L. E.; Robichaud, A. J. Bioorg. Med. Chem. Lett. 2009, 19, 1115.
[5]	Muro, F.; Iimura, S.; Yoneda, Y.; Chiba, J.; Watanabe, T.; Setoguchi, M.; Takayama, G.; Yokoyama, M.; Takashi, T.; Nakayama, A.; Machinaga, N. Bioorg. Med. Chem. 2009, 17, 1232.
[6]	Kablaoui, N.; Patel, S.; Shao, J.; Demian, D.; Hoffmaster, K.; Berlioz, F.; Vazquez, M. L.; Moore, W. M.; Nugent, R. A. Bioorg. Med. Chem. Lett. 2013, 23, 907. doi: 10.1016/j.bmcl.2012.10.040 pmid: 23266122
[7]	Seregin, I.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173. doi: 10.1039/b606984n pmid: 17576484
[8]	You, L.; Yuan, J.; Yang, L.; Xiao, Y.; Mao, P. Chin. J. Org. Chem. 2016, 36, 2634 (in Chinese).
	(游利琴, 袁金伟, 杨亮茹, 肖咏梅, 毛璞, 有机化学, 2016, 36, 2634.) doi: 10.6023/cjoc201604044
[9]	(a) Vardhan Reddy, K. H.; Anil Kumar, B. S. P.; Prakash Reddy, V.; Uday Kumar, R.; Nageswar, Y. V. D. RSC Adv. 2014, 4, 45579.
	(b) Yamato, M.; Takeuchi, Y.; Hattori, K.; Hashigaki, K. Chem. Pharm. Bull. 1984, 32, 3053.
	(c) Saladino, R.; Crestini, C.; Occhionero, F.; Nicoletti, R. Synth. Commun. 1996, 26, 3241.
	(d) Kövér, J.; Tímár, T.; Tompa, J. Synthesis 1994, 1124.
	(e) Gu, J.; Cai, C. Synlett 2015, 26, 639.
[10]	(a) Wu, Y. Q.; Limburg, D. C.; Wilkinson, D. E.; Hamilton, G. S. J. Heterocycl. Chem. 2003, 40, 191.
	(b) El-Faham, A.; Chebbo, M.; Abdul-Ghani, M.; Younes, G. Heterocycl. Chem. 2006, 43, 599.
	(c) Cioffi, C. L.; Lansing, J. J.; Yüksel, H. J. Org. Chem. 2010, 75, 7942.
	(d) Zhang, X. Y.; Jia, X. F.; Wang, J. J.; Fan, X. S. Green Chem. 2011, 13, 413.
	(e) Kasthuri, M.; Sharath Babu, H.; Shiva Kumar, C.; Nagendra Kumar, P. V. Synlett 2015, 26, 897.
	(f) Lin, C. C.; Hsieh, T. H.; Liao, P. Y.; Liao, Z. Y.; Chang, C. W.; Shih, Y. C.; Yeh, W. H.; Chien, T. C. Org. Lett. 2014, 16, 892.
[11]	(a) Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem.,Int. Ed. 2010, 49, 9899. pmid: 19254040
	(b) Li, Y. M.; Liu, J.; Xie, Y. S.; Zhang, R.; Jin, K.; Wang, X. N.; Duan, C. Y. Org. Biomol. Chem. 2012, 10, 3715. pmid: 19254040
	(c) Li, Y. M.; Xie, Y. S.; Zhang, R.; Jin, K.; Wang, X. N.; Duan, C. Y. J. Org. Chem. 2011, 76, 5444. pmid: 19254040
	(d) Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607. doi: 10.1021/ol900298e pmid: 19254040
	(e) Pal, P.; Giri, A. K.; Singh, H.; Ghosh, S. C.; Panda, A. B. Chem. Asian J. 2014, 9, 2392. pmid: 19254040
	(f) Xie, Y. J.; Qian, B.; Xie, P.; Huang, H. M. Adv. Synth. Catal. 2013, 355, 1315. pmid: 19254040
	(g) Gao, W. J.; Li, W. C.; Zeng, C. C.; Tian, H. Y.; Hu, L. M.; Little, R. D. J. Org. Chem. 2014, 79, 9613. pmid: 19254040
[12]	(a) Gilchrist, T. L.; John Harris, C.; King, F. D.; Peek, M. E. J. Chem. Soc., 1988, 2169. pmid: 25641711
	(b) Morofuji, T.; Shimizu, A.; Yoshida, J. Chem.-Eur. J. 2015, 21, 3211. doi: 10.1002/chem.201406398 pmid: 25641711
[13]	(a) Wang, H.; Xu, B. Chin. J. Org. Chem. 2015, 35, 588 (in Chinese).
	(王浩, 许斌, 有机化学, 2015, 35, 588.) doi: 10.6023/cjoc201411035
	(b) Lv, Y.; Bao, P.; Yue, H.; Li, J-S.; Wei, W. Green Chem. 2019, 21, 6051.
	(c) Ma, C.; Li, X.; Chen, X.; He, X.; Zhang, S-T.; Jiang, Y-Q.; Yu, B. Org. Lett., 2023, 25, 8016.
[14]	(a) Zhu, T.-H.; Wang, S.-Y.; Wang, G.-N.; Ji, S.-J. Chem.-Eur. J. 2013, 19, 5850.
	(b) Zhu, T.-H.; Wang, S.-Y.; Wang, G.-N.; Ji, S.-J. Adv. Synth. Catal. 2014, 356, 509.
[15]	Liu, J.; Hoover, J. M. Org. Lett. 2019, 21, 4510.
[16]	Liu, B.; Yin, M.; Gao, H.; Wu, W.; Jiang, H. J. Org. Chem. 2013, 78, 3009.
[17]	Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058.
[18]	Wang, G.-N.; Zhu, T.-H.; Wang, S.-Y.; Wei, T.-Q.; Ji, S.-J. Tetrahedron 2014, 70, 8079.
[19]	(a) Ji, H.-T.; Jiang, J.; He, W.-B.; Lu, Y.-H.; Liu, Y.-Y.; Li, X.; He, W-M. J. Org. Chem. 2024, 89, 4113. pmid: 12027681
	(b) Ji, H.-T.; Luo, Q.-X.; Wang, K.-L.; Ouyang, W.-T.; Li, H.-X.; He, W.-M. Green Chem. 2023, 25, 7983. pmid: 12027681
	(c) Kihlberg, T.; Karimi, F.; Långström, B. J. Org. Chem. 2002, 67, 3687. pmid: 12027681
[20]	(a) Fei, N.; Wang, Y.; Gu, Y.; Wang, Z.; Zhu, Y.; Li, Y. J. Org. Chem. 2023, 88, 13042.
	(b) Lin, J.-X.; Liu, G.-H.; Liu, L.-Q.; Wang, Y.-C.; He, Y. J. Org. Chem. 2024, 89, 101.
	(c) Zhong, W.; Li, M.; Jin, Y.; Jiang, H.; Wu, W. Chem. Commun. 2022, 58, 6522.
	(d) Shao, L.; Li, Y.; Lu, J.; Jiang, X. Org. Chem. Front. 2019, 6, 2999.
[21]	(a) Duangkamol, C.; Phakhodeea, W.; Pattarawarapan, M. Synthesis 2020, 52, 1981.
	(b) Tran, D. T.; Huynh, T. N.; Nguyen, P. C.; Phan, N. T. S.; Nguyen, T. T. Tetrahedron Lett. 2023, 122, 154510.
	(c) Xu, Y.; Li, F.; Zhao, N.; Su, J.; Wang, C.; Wang, C.; Li, Z.; Wang, L. Green Chem. 2021, 23, 8047.

Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	K₂CO₃ (1)	DCM	25	23
2	Cs₂CO₃ (1)	DCM	25	5
3	Na₂CO₃ (1)	DCM	25	25
4	K₃PO₄ (1)	DCM	25	26
5	^tBuONa (1)	DCM	25	65
6	DABCO (1)	DCM	25	33
7	Et₃N (1)	DCM	25	26
8	DBU (1)	DCM	25	21
9	^tBuONa (1)	EtOH	25	30
10	^tBuONa (1)	DMF	25	61
11	^tBuONa (1)	1,4-Dioxane	25	20
12	^tBuONa (1)	CH₃CN	25	56
13	^tBuONa (1)	EtOAc	25	0
14	^tBuONa (1)	Toluene	25	0
15	^tBuONa (1)	DMSO	25	76
16	^tBuONa (0.2)	DMSO	25	38
17	—	DMSO	25	trace
18	^tBuONa (1)	DMSO	60	88
19	^tBuONa (1)	DMSO	80	86
20	^tBuONa (1)	DMSO	60	62^c
21	^tBuONa (1)	DMSO	60	21^d
22	^tBuONa (1)	DMSO	60	0^e

Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	K₂CO₃ (1)	DCM	25	23
2	Cs₂CO₃ (1)	DCM	25	5
3	Na₂CO₃ (1)	DCM	25	25
4	K₃PO₄ (1)	DCM	25	26
5	^tBuONa (1)	DCM	25	65
6	DABCO (1)	DCM	25	33
7	Et₃N (1)	DCM	25	26
8	DBU (1)	DCM	25	21
9	^tBuONa (1)	EtOH	25	30
10	^tBuONa (1)	DMF	25	61
11	^tBuONa (1)	1,4-Dioxane	25	20
12	^tBuONa (1)	CH₃CN	25	56
13	^tBuONa (1)	EtOAc	25	0
14	^tBuONa (1)	Toluene	25	0
15	^tBuONa (1)	DMSO	25	76
16	^tBuONa (0.2)	DMSO	25	38
17	—	DMSO	25	trace
18	^tBuONa (1)	DMSO	60	88
19	^tBuONa (1)	DMSO	80	86
20	^tBuONa (1)	DMSO	60	62^c
21	^tBuONa (1)	DMSO	60	21^d
22	^tBuONa (1)	DMSO	60	0^e

硒介导异腈与邻氨基苯酚环化反应合成2-胺基苯并噁唑