Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles

doi:10.6023/cjoc201711015

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3242-3247.DOI: 10.6023/cjoc201711015 Previous Articles Next Articles

Articles

碘催化的咪唑类化合物N-H键的官能化

杨丽烽, 惠人杰, 单恒悦, 巩凯

江南大学药学院无锡 214122

收稿日期:2017-11-08 修回日期:2017-12-04 发布日期:2017-12-08
通讯作者: 巩凯 E-mail:gongkai@jiangnan.edu.cn
基金资助:
国家自然科学基金（No.51303069）、江苏高校品牌专业建设工程（No.PPZY2015B146）资助项目.

Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles

Yang Lifeng, Hui Renjie, Shan Hengyue, Gong Kai

School of Pharmaceutical Science, Jiangnan University, Wuxi 214122

Received:2017-11-08 Revised:2017-12-04 Published:2017-12-08
Contact: 10.6023/cjoc201711015 E-mail:gongkai@jiangnan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51303069), and the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions (No. PPZY2015B146).

1. Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles.PDF(1003KB)

Abstract

Since benzimidazole containing moieties have a lot of pharmacological activities, we reported the ageneral metal-free and cost-effective, I₂/DTBP-catalyzed method for the functionalization of N-H bonds of azoles via α-C(sp³)-H activation of cyclic ethers or cyclic thioethers. And this method is also applicable to a diverse range of N-substituted azoles and cyclic ethers/thioethers. By using the free-radical scavenger 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) as a control, we suggest that a radical/SET mechanism proceeding via a radical/oxonium or thionium ion may be involved in the reaction.

Key words: iodine, functionalization of N-H bond, cyclic ether, cross dehydrogenative coupling, cyclic thioether

Cite this article

Yang Lifeng, Hui Renjie, Shan Hengyue, Gong Kai. Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles[J]. Chin. J. Org. Chem., 2017, 37(12): 3242-3247.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
(b) Collet, F.; Dodd, R.; Dauban, P. Chem. Commun. 2009, 5061.
(c) Zalatan, D.; Bois, J. D. Top. Curr. Chem. 2010, 292, 347.
(d) Bois, J. D. Org. Process Res. Dev. 2011, 15, 758.
(e) Gephart, R. T.; Warren, T. H. Organometallics 2012, 31, 7728.
[2] (a) Liao, C. L.; Shi, J. J.; Liang, P. H.; Wong, C. H. Chem. Biol. 2006, 13, 261.
(b) Ren, Y.; Zhang, L.; Zhou, C. H.; Geng, R. X. Med. Chem. 2014, 4, 640.
(c) Rad, M. N. S.; Khalafi-Nezhad, A.; Behrouz, S. Beilstein J. Org. Chem. 2010, 6, 49.
(d) Zhang, H. Z.; Damu, G. L. V.; Cai, G. X.; Zhou, C. H. Eur. J. Med. Chem. 2013, 64, 329.
(e) Rezaei, Z.; Khabnadideh, S.; Pakshir, K.; Hossaini, Z.; Amiri, F.; Assadpour, E. Eur. J. Med. Chem. 2009, 44, 3064.
(f) Sharma, D.; Narasimhan, B.; Kumar, P.; Jalbout, A. Eur. J. Med. Chem. 2009, 44, 1119.
(g) Santo, R. D.; Tafi, A.; Costi, R.; Botta, M.; Artico, M.; Corelli, F.; Forte, M.; Caporuscio, F.; Angiolella, L.; Palamara, A. T. J. Med. Chem. 2005, 48, 5140.
(h) Rossello, A.; Bertini, S.; Lapucci, A.; Macchia, M.; Martinelli, A.; Rapposelli, S.; Herreros, E.; Macchia, B. J. Med. Chem. 2002, 45, 4903.
(i) Dubey, A.; Srivastava, S. K.; Srivastava, S. D. Bioorg. Med. Chem. Lett. 2011, 21, 569.
(j) Giornal, F.; Pazenok, S.; Rodefeld, L.; Lui, N.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2013, 152, 2.
[3] (a) Li, F.; Hu, J. J.; Koh, L. L.; Hor, T. S. A. Dalton Trans. 2010, 39, 5231.
(b) Huckaba, A. J.; Hollis, T. K.; Howell, T. O.; Valle, H. U.; Wu, Y. Organometallics 2013, 32, 63.
(c) Gupta, S.; Basu, B.; Das, S. Tetrahedron 2013, 69, 122.
(d) Kore, R.; Srivastava, R. J. Mol. Catal. A:Chem. 2011, 345, 117.
(e) Tsuji, Y.; Ohno, H. RSC Adv. 2012, 2, 11279.
[4] (a) Milen, M.; Gru?n, A.; Ba?lint, E.; Dancso?, A.; Keglevich, G. Synth. Commun. 2010, 40, 2291.
(b) Shieh, W. C.; Lozanov, M; Repic?, O. Tetrahedron Lett. 2003, 44, 6943.
(c) Hayat, S.; Attaur-Rahman; Choudhary, M. I.; Khan, K. M.; Schumann, W.; Bayer, E. Tetrahedron 2001, 57, 9951.
[5] (a) Guo, S.; Yu, J. T.; Dai, Q.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 6240.
(b) Jia, Z.; Nagano, T.; Li, X.; Chan, A. S. C. Eur. J. Org. Chem. 2013, 858.
(c) Chu, X. Q.; Meng, H.; Zi, Y.; Xu, X. P.; Ji, S. J. Chem. Commun. 2014, 50, 9718.
(d) Majji, G.; Guin, S.; Gogoi, A.; Rout, S. K.; Patel, B. K. Chem. Commun. 2013, 49, 3031.
(e) Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384.
(f) Zhang, S.; Guo, L. N.; Wang, H.; Duan, X. H. Org. Biomol. Chem. 2013, 11, 4308.
(g) Huang, J.; Li, L. T.; Li, H. Y.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204.
(h) Zhang, X.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2014, 50, 8006.
(i) Xue, Q.; Xie, J.; Li, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 3700.
(j) Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751.
(k) Chen, S.; Xu, Y.; Wan, X. Org. Lett. 2011, 13, 6152.
(l) Froehr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.; Nachtsheim, B. J. Org. Lett. 2011, 13, 754.
(m) Mai, W. P.; Song, G.; Yuan, J. W.; Yang, L. R.; Sun, G. C.; Xiao, Y. M.; Mao, P.; Qu, L. B. RSC Adv. 2013, 3, 3869.
(n) Lv, Y.; Li, Y.; Xiong, T.; Lu, Y.; Liu, Q.; Zhang, Q. Chem. Commun. 2014, 50, 2367.
[6] Pan, S.; Liu, J.; Li, H.; Wang, Z.; Guo, X.; Li, Z. Org. Lett. 2010, 12, 1932.
[7] (a) Buslova, I.; Hua, X. L. Adv. Synth. Catal. 2014, 356, 3325.
(b) Aruri, H.; Singh, U.; Sharma, S.; Gudup, S.; Bhogal, M.; Kumar, S.; Singh, D.; Gupta, V. K.; Kant, R.; Vishwakarma, R. A.; Singh, P. P. J. Org. Chem. 2015, 80, 1929.
[8] (a) Hao, W. J.; Wang, S. Y.; Ji, S. J. ACS Catal. 2013, 3, 2501.
(b) Sun, J.; Qiu, J. K.; Zhu, Y. L.; Guo, C.; Hao, W. J.; Jiang, B.; Tu, S. J. J. Org. Chem. 2015, 80, 8217.
(c) von der Heiden, D.; Bozkus, S.; Klussmann, M.; Breugst, M. J. Org. Chem. 2017, 82, 4037.
(d) Zhang, Z.; Pi, C.; Tong, H.; Cui, X.; Wu, Y. Org. Lett. 2017, 19, 440.
(e) Wang, B.; Meng, Y.; Zhou, Y.; Ren, L.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2017, 82, 5898.
(f) Yuan, S. T.; Wang, Y. H.; Qiu, G. Y. S.; Liu, J. B. Chin. J. Org. Chem. 2017, 37, 566(in Chinese). (袁斯甜, 王艳华, 邱观音生, 刘晋彪, 有机化学, 2017, 37, 566.)
(g) Duan, Y. N.; Jiang, S.; Han, Y. C.; Sun, B.; Zhang, C. Chin. J. Org. Chem. 2016, 36, 1973(in Chinese). (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
[9] (a) Yang, D.; Yan, K.; Wei, W.; Zhao, J.; Zhang, M.; Sheng, X.; Li, G.; Lu, S.; Wang, H. J. Org. Chem. 2015, 80, 6083.
(b) Beukeaw, D.; Udomsasporn, K.; Yotphan, S. J. Org. Chem. 2015, 80, 3447.
(c) Luo, W. K.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18, 2036.
(d) Wang, Y.; Jiang, C. M.; Li, H. L.; He, F. S.; Luo, X.; Deng, W. P. J. Org. Chem. 2016, 81, 8653.
(e) Siddaraju, Y.; Prabhu, K. R. J. Org. Chem. 2017, 82, 3084.
(f) Fan, W.; Yang, Z.; Jiang, B.; Li, G. Org. Chem. Front. 2017, 4, 1091.
(g) Fan, W.; Li, Q.; Li, Y.; Sun, H.; Jiang, B.; Li, G. Org. Lett. 2016, 18, 1258.
(h) Yang, D.; Sun, P.; Wei, W.; Meng, L.; He, L.; Fang, B.; Jiang, W.; Wang, H. Org. Chem. Front. 2016, 3, 1457.
(i) Wu, W.; An, Y.; Li, J.; Yang, S.; Zhu, Z.; Jiang, H. Org. Chem. Front. 2017, 4, 1751.
(j) Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 3127.
[10] Cheng, D.; Wu, L.; Lv, H.; Xu, X.; Yan, J. J. Org. Chem. 2017, 82, 1610 and references cited therein.

[1]	Tongyang Cao, Wei Li, Lijing Wang. Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 508-524.
[2]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[3]	Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.
[4]	Yu Zhao, Yurong Duan, Shihui Shi, Yubin Bai, Liangzhu Huang, Xiaojun Yang, Yantu Zhang, Bin Feng, Jianbo Zhang, Qiuyu Zhang. Recent Advances of Hypervalent Iodine(III) Reagents upon Visible Light Irradiation [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4106-4140.
[5]	Haojie Ma, Fengyuan Zhou, Fanwen Su, Bo Han, Ran Li, Yuqi Zhang, Jijiang Wang. Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3960-3965.
[6]	Qianmin Li, Manman Wang, Wenquan Yu, Junbiao Chang. Synthesis of β-Nitroamines and α-Aminonitriles by I₂-Mediated Oxidative C—C Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3966-3976.
[7]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[8]	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.
[9]	Jiajia Lu, Junli Yang, Jie Gu, Ju Yang, Zhenjie Gao, Lijiao Su, Xin Tao, Mingwei Yuan, Lijuan Yang. Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^– [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1474-1482.
[10]	Fufang Wu, Xuejian Li, Hao Jia, Xuanzhen Han, Xiaobao Shen. Iodine(III)-Promoted Oxidative Cross-Coupling Reactions of C—H Bonds via a Free Radical Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 884-890.
[11]	Ruiqin Zhang, Renchao Ma, Qinjiao Fu, Jing Chen, Yongmin Ma. I₂/PhNO₂ Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 854-862.
[12]	Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.
[13]	Zhifang Yang, Yifu Cheng, Beibei Zhang, Yunyi Dong, Chi Han, Yunfei Du. Oxidative Rearrangement Reactions Mediated by Hypervalent-Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3456-3505.
[14]	Ruikai Liu, Zheng Xu, Zhitao Ning, Zhengyin Du. Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 200-207.
[15]	Tingxun Yan, Chao Chen, Lirong Wen. Study on the Selective Difluorochloroethylation Reactions of Amides with Hypervalent Iodine Reagent [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3660-3667.

碘催化的咪唑类化合物N-H键的官能化

Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments