重氮化反应高效合成1H-吲唑-3-羧酸衍生物
收稿日期: 2021-03-04
修回日期: 2021-04-06
网络出版日期: 2021-05-08
基金资助
国家自然科学基金(21662024); 国家自然科学基金(22061025); 甘肃省自然科学基金(20JR10RA220); 兰州交通大学百名青年人才培训计划资助项目
Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction
Received date: 2021-03-04
Revised date: 2021-04-06
Online published: 2021-05-08
Supported by
National Natural Science Foundation of China(21662024); National Natural Science Foundation of China(22061025); Natural Science Foundation of Gansu Province(20JR10RA220); Foundation of a Hundred Youth Talents Training Program of Lanzhou Jiaotong University
报道了邻氨基苯乙酰胺和邻氨基苯乙酸酯在重氮化试剂作用下直接转化为对应的1H-吲唑-3-羧酸衍生物. 该反应操作简单, 反应条件温和, 反应迅速, 产率高, 底物范围广, 为1H-吲唑-3-羧酸衍生物的合成提供了一种更加高效简洁的新方法. 该方法被成功应用于药物分子格拉司琼和氯尼达明的合成, 分别以46%和60%的总收率得到了目标产物. 初步的机理研究表明重氮盐是该反应的关键中间体.
关键词： 1H-吲唑-3-羧酸衍生物; 重氮化; 格拉司琼; 氯尼达明
徐长明 , 黄金程 . 重氮化反应高效合成1H-吲唑-3-羧酸衍生物[J]. 有机化学, 2021 , 41(8) : 3256 -3263 . DOI: 10.6023/cjoc202103008
Direct conversion of ortho-aminobenzacetamides and ortho-aminobenzacetates to the corresponding 1H-indazole- 3-carboxylic acid derivatives under the action of diazotization reagents was reported. This method features operational simplicity, mild reaction conditions, rapid reaction rates, high yields, wide substrate scope, offering an efficient and concise route to synthesis of 1H-indazole-3-carboxylic acid derivatives. The drugs granisetron and lonidamine were synthesized successfully using this protocol with 46% and 60% total yields, respectively. Preliminary mechanistic study suggests that diazonium salt is a key intermediate.
| [1] | For selected reviews, see: |
| [1] | (a) Schmidt, A.; Beutler, A.; Snovydovych, B. Eur. J. Org. Chem. 2008, 4073. |
| [1] | (b) Ghosh, S.; Mondal, S.; Hajra, A. Adv. Synth. Catal. 2020, 362, 3768. |
| [1] | For selected examples, see: |
| [1] | (c) Zhang, X.; Pan, Y.; Liang, P.; Ma, X.; Jiao, W.; Shao, H. Adv. Synth. Catal. 2019, 361, 5552. |
| [1] | (d) Hunter, C. J.; Boyd, M. J.; May, G. D.; Fimognari, R. J. Org. Chem. 2020, 85, 8732. |
| [2] | Vernekar, S. K. V.; Hallaq, H. Y.; Clarkson, G.; Thompson, A. J.; Silvestri, L.; Lummis, S. C. R.; Lochner, M. J. Med. Chem. 2010, 53, 2324. |
| [3] | Gatto, M. T.; Tita, B.; Artico, M.; Saso, L. Contraception 2002, 65, 277. |
| [4] | Kuang, S.-M.; Zhang, P. US 20110172428, 2011. |
| [5] | Nakano, H.; Hasegawa, T.; Imamura, R.; Saito, N.; Kojima, H.; Okabe, T.; Nagano, T. Bioorg. Med. Chem. Lett. 2016, 26, 2370. |
| [6] | Snyder, H. R.; Thompson, C. B.; Hinman, R. L. J. Am. Chem. Soc. 1952, 74, 2009. |
| [7] | Xiong, X.; Jiang, Y.; Ma, D. Org. Lett. 2012, 14, 2552. |
| [8] | (a) Ferrari, M.; Ripa, A.; Ripa, G. Sisti, M. J. Heterocycl. Chem. 1989, 26, 531. |
| [8] | (b) Han, B.; Yang, F.; Wang, L. CN 104370888, 2015. |
| [9] | Yoshida, T.; Matsuura, N.; Yamamoto, K.; Doi, M.; Shimada, K.; Morie, T.; Kato, S. Heterocycles 1996, 43, 2701. |
| [10] | Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 3323. |
| [11] | Alaime, T.; Daniel, M.; Hiebel, M.-A.; Pasquinet, E.; Suzenet, F.; Guillaumet, G. Chem. Commun. 2013, 54, 8411. |
| [12] | (a) Wang, H.; Zhao, Z. CN 103787978, 2014. |
| [12] | (b) Tang, M.; Kong, Y.; Chu, B.; Feng, D. Adv. Synth. Catal. 2016, 358, 926. |
| [12] | (c) Tang, M.; Kong, Y.; Chu, B. CN 106316958, 2017. |
| [13] | (a) Rüchardt, C.; Hassmann, V. Liebigs Ann. Chem. 1980, 908. |
| [13] | (b) Bartsch, R.; Yang, I.-W. J. Heterocycl. Chem. 1984, 21, 1063. |
| [13] | (c) Schumann, P.; Collot, V.; Hommet, Y.; Gsell, W.; Dauphin, F.; Sopkova, J.; MacKenzie, E. T.; Duval, D.; Boulouard, M.; Rault, S. Bioorg. Med. Chem. Lett. 2001, 11, 1153. |
| [14] | Zhu, J.; Mao, J.; Yang, M.; Wu, X. CN 102911174, 2013. |
| [15] | For selected examples, see: |
| [15] | (a) Bermudez, J.; Fake, C. S.; Joiner, G. F.; Joiner, K. A.; King, F. D.; Miner, W. D.; Sanger, G. J. J. Med. Chem. 1990, 33, 1924. |
| [15] | (b) Mu, L.; Muller Herde, A.; Ruefli, P. M.; Sladojevich, F.; Milicevic Sephton, S.; Kramer, S. D.; Thompson, A. J.; Schibli, R.; Ametamey, S. M.; Lochner, M. ACS Chem. Neurosci. 2016, 7, 1552. |
| [15] | (c) Coomber, C. E.; Laserna, V.; Martin, L. T.; Smith, P. D.; Hailes, H. C.; Portera, M. J.; Sheppard, T. D. Org. Biomol. Chem. 2019, 17, 6465. |
| [15] | (d) Opie, C. R.; Noda, H.; Shibasaki, M.; Kumagai, N. Chem-Eur. J. 2019, 25, 4648. |
| [16] | (a) Dalmases Barjoan, P.; Puig Torres, S. WO 2003080606, 2003. |
| [16] | (b) Ward, N.; Jones, D. A.; Jacewicz, V. W. WO 9730049, 1997. |
| [17] | SmithKline Beecham PLC, AT406770, 2000. |
| [18] | Xie, Y.; Zhang, S.; Ge, X.; Ma, W.; He, X.; Zhao, Y.; Ye, J.; Zhang, H.; Wang, A.; Liu, Z. Appl. Organomet. Chem. 2020, 34, e5589. |
| [19] | (a) Yin, J.; Xia, M.; Dong, H.; Ding, F.; Xu, S. CN 103159679, 2013. |
| [19] | (b) Liu, C.; Dong, Z.; Zhang, W.; Tang, P.; Gao, J. CN 1594297, 2005. |
| [19] | (c) Hou, C.-J.; Luo, B.; Huo, D.-Q. Prog. Pharm. Sci. 2006, 30, 235. (in Chinese) |
| [19] | (侯长军, 罗斌, 霍丹群, 药学进展, 2006, 30, 235.) |
| [20] | Senadi, G. C.; Wang, J.-Q.; Gore, B. S.; Wang, J.-J. Adv. Synth. Catal. 2017, 359, 2747. |
| [21] | (a) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1994, 50, 3529. |
| [21] | (b) Zhao, X.; Liu, Q.; Feng, R.; Zeng, X.; Wentrup, C. Eur. J. Org. Chem. 2019, 2019, 6945. |
| [22] | Buchstaller, H.-P.; Wilkinson, K.; Burek, K.; Nisar, Y. Synthesis 2011, 3089. |
/
| 〈 |
|
〉 |
