硒介导异腈与邻氨基苯酚环化反应合成2-胺基苯并噁唑

doi:10.6023/cjoc202407001

摘要/Abstract

报道了一种硒粉介导下异腈与邻氨基苯酚进行环化反应合成2-胺基苯并噁唑的方法. 该反应简单地采用硒粉为促进剂, 叔丁醇钠作为碱,在温和条件下实现了多种2-胺基苯并噁唑的绿色、高效构建. 该反应具有操作简便和无金属污染的优点. 该方法还可以实现2-胺基苯并噻唑和2-胺基苯并咪唑的合成.

关键词: 非金属, 硒, 异腈, 邻氨基苯酚, 2-胺基苯并噁唑

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

引用此文

王峥, 兰羽琴, 周芷怡, 谭英姿, 王宗成. 硒介导异腈与邻氨基苯酚环化反应合成2-胺基苯并噁唑[J]. 有机化学, doi: 10.6023/cjoc202407001.

Wang Zheng, Lan Yuqin, Zhou Zhiyi, Tan Yingzhi, Wang Zongcheng. Selenium Mediated Cyclization Reaction of Isonitriles with o-Aminophenols to Synthesize 2-Aminobenzoxazoles[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202407001.

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参考文献

[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.
(b) Safak C.; Erdogan H.; Palaska E.; Sunal R.; Duru, S. J. Med. Chem.1992, 35, 1296.
(c) Feng M. H.; Tang B. Q.; Liang S. H.; Jiang, X. F. Curr. Top. Med. Chem.2016, 16, 1200.
(d) Hal I. H.; Peaty N. J.; Henry J. R.; Easmon J.; Heinisch G.; Pürstinger G. Arch. Pharm.1999, 332, 115.
(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
(f) Chen, X.; Ouyang, W-T.; Li, X.; He, W-M.Chin. J. Org. Chem. 2023, 43, 4213.
(陈祥, 欧阳文韬, 李潇, 何卫民, 有机化学, 2023, 43, 4213).
[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.
(b) Kohler P. C.; Ritschel T.; Schweizer W. B.; Klebe G.; Diederich, F. Chem. -Eur. J.2009, 15, 10809.
(c) Liu, K. G.; Lo, J. R.; Comery, T. A.; Zhang, G. M.; Zhang, J. Y.; Kowal, D. M.; Smith, D. L.; Kerns, E. H.; Schechter, L. E.; Robichaud, A. J.Bioorg. Med. Chem. Lett. 2009, 19, 1115.
[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. Bio. 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.
[7] Seregin I.; Gevorgyan, V. Chem. Soc. Rev.2007, 36, 1173.
[8] You L.; Yuan J.; Yang L.; Xiao Y.; Mao, P. Chin. J. Org. Chem.2016, 36, 2634.
(游利琴, 袁金伟, 杨亮茹, 肖咏梅, 毛璞, 有机化学, 2016, 36, 2634).
[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.
(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.
(c) Li Y. M.; Xie Y. S.; Zhang R.; Jin K.; Wang X. N.; Duan, C. Y. J. Org. Chem.2011, 76, 5444.
(d) Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A.Org. Lett. 2009, 11, 1607.
(e) Pal, P.; Giri, A. K.; Singh, H.; Ghosh, S. C.; Panda, A. B.Chem. Asian J. 2014, 9, 2392.
(f) Xie, Y. J.; Qian, B.; Xie, P.; Huang, H. M.Adv. Synth. Catal. 2013, 355, 1315.
(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.
[12] (a) Gilchrist, T. L.; John Harris, C.; King, F. D.; Peek, M. E.J. Chem. Soc., Perkin Trans. 1 1988, 2169.
(b) Morofuji T.; Shimizu A.; Yoshida, J. Chem. Eur. J.2015, 21, 3211.
[13] (a) Wang H.; Xu, B. Chin. J. Org. Chem.2015, 35, 588.
(王浩, 许斌, 有机化学, 2015, 35, 588-602).
(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, 5850-5853.
(b) Zhu T-H.; Xu X-P.; Cao J-J.; Wei,T-Q.; Wang S-Y.; 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. Tetrahedron2014, 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.
(b) Ji H-T.; Luo Q-X.; Wang K-L.; Ouyang W-T.; Li H-X.; He W-M. Green Chem.2023, 25, 7983.
(c) Kihlberg T.; Karimi F.; Långström, B. J. Org. Chem.2002, 67, 3687.
[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.