Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction

doi:10.6023/cjoc202103008

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3256-3263.DOI: 10.6023/cjoc202103008 Previous Articles Next Articles

ARTICLES

重氮化反应高效合成1H-吲唑-3-羧酸衍生物

徐长明^*(), 黄金程

兰州交通大学化学化工学院兰州 730070

收稿日期:2021-03-04 修回日期:2021-04-06 发布日期:2021-05-08
通讯作者: 徐长明
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

Changming Xu(), Jincheng Huang

School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou 730070

Received:2021-03-04 Revised:2021-04-06 Published:2021-05-08
Contact: Changming Xu
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

1. .pdf(5049KB)

Abstract

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.

Key words: 1H-indazole-3-carboxylic acid derivatives, diazotization, granisetron, lonidamine

Cite this article

Changming Xu, Jincheng Huang. Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3256-3263.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Scheme 1. Synthetic methods of 1H-indazole-3-carboxylic acid derivatives

Table 1. Scope of substrates

Scheme 2. Synthetic route to Granisetron

Scheme 3. Synthetic route to Lonidamine

Scheme 4. Mechanism exploration of diazotization reaction

Scheme 5. Proposed mechanism of diazotization reaction

References 22

[1]	(d) Hunter, C. J.; Boyd, M. J.; May, G. D.; Fimognari, R. J. Org. Chem. 2020, 85, 8732. doi: 10.1021/acs.joc.0c00983
[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. doi: 10.1021/jm901827x pmid: 20146481
[3]	Gatto, M. T.; Tita, B.; Artico, M.; Saso, L. Contraception 2002, 65, 277. doi: 10.1016/S0010-7824(02)00289-5
[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. doi: 10.1016/j.bmcl.2016.03.006
[6]	Snyder, H. R.; Thompson, C. B.; Hinman, R. L. J. Am. Chem. Soc. 1952, 74, 2009. doi: 10.1021/ja01128a042
[7]	Xiong, X.; Jiang, Y.; Ma, D. Org. Lett. 2012, 14, 2552. doi: 10.1021/ol300847v
[8]	(a) Ferrari, M.; Ripa, A.; Ripa, G. Sisti, M. J. Heterocycl. Chem. 1989, 26, 531. doi: 10.1002/jhet.v26:2
	(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. doi: 10.3987/COM-96-7614
[10]	Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 3323. doi: 10.1002/(ISSN)1521-3773
[11]	Alaime, T.; Daniel, M.; Hiebel, M.-A.; Pasquinet, E.; Suzenet, F.; Guillaumet, G. Chem. Commun. 2013, 54, 8411. doi: 10.1039/C8CC03612H
[12]	(a) Wang, H.; Zhao, Z. CN 103787978, 2014.
	(b) Tang, M.; Kong, Y.; Chu, B.; Feng, D. Adv. Synth. Catal. 2016, 358, 926. doi: 10.1002/adsc.v358.6
	(c) Tang, M.; Kong, Y.; Chu, B. CN 106316958, 2017.
[13]	(a) Rüchardt, C.; Hassmann, V. Liebigs Ann. Chem. 1980, 908. pmid: 11354365
	(b) Bartsch, R.; Yang, I.-W. J. Heterocycl. Chem. 1984, 21, 1063. doi: 10.1002/jhet.v21:4 pmid: 11354365
[1]	For selected reviews, see:
	(a) Schmidt, A.; Beutler, A.; Snovydovych, B. Eur. J. Org. Chem. 2008, 4073.
	(b) Ghosh, S.; Mondal, S.; Hajra, A. Adv. Synth. Catal. 2020, 362, 3768. doi: 10.1002/adsc.v362.18
	For selected examples, see:
	(c) Zhang, X.; Pan, Y.; Liang, P.; Ma, X.; Jiao, W.; Shao, H. Adv. Synth. Catal. 2019, 361, 5552. doi: 10.1002/adsc.v361.24
[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. pmid: 11354365
[14]	Zhu, J.; Mao, J.; Yang, M.; Wu, X. CN 102911174, 2013.
[15]	For selected examples, see: pmid: 2362270
	(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. pmid: 2362270
	(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. doi: 10.1021/acschemneuro.6b00192 pmid: 2362270
	(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. doi: 10.1039/C9OB01012B pmid: 2362270
	(d) Opie, C. R.; Noda, H.; Shibasaki, M.; Kumagai, N. Chem-Eur. J. 2019, 25, 4648. doi: 10.1002/chem.v25.18 pmid: 2362270
[16]	(a) Dalmases Barjoan, P.; Puig Torres, S. WO 2003080606, 2003.
	(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.
	(b) Liu, C.; Dong, Z.; Zhang, W.; Tang, P.; Gao, J. CN 1594297, 2005.
	(c) Hou, C.-J.; Luo, B.; Huo, D.-Q. Prog. Pharm. Sci. 2006, 30, 235. (in Chinese)
	(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. doi: 10.1002/adsc.v359.16
[21]	(a) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1994, 50, 3529. doi: 10.1016/S0040-4020(01)87030-7
	(b) Zhao, X.; Liu, Q.; Feng, R.; Zeng, X.; Wentrup, C. Eur. J. Org. Chem. 2019, 2019, 6945. doi: 10.1002/ejoc.201901271
[22]	Buchstaller, H.-P.; Wilkinson, K.; Burek, K.; Nisar, Y. Synthesis 2011, 3089.

重氮化反应高效合成1H-吲唑-3-羧酸衍生物

Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 22

Related Articles 5

Recommended Articles

Metrics

Comments

[1]	Runhong Jia, Shuai Liu, Shichao Wang, Wenjuan Hao, Bo Jiang. A Solvent-Regulated Dediazotized Oxygenation of α-Aryl α-Diazoesters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2814-2822.
[2]	Li Qingxue, Li Mengwei, Shi Shaoqing, Ji Xiaoshuang, He Chunlan, Jiang Bo, Hao Wenjuan. PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 384-390.
[3]	Han Peng;Wang Xiaowei;Zhang Zhili;Liu Junyi. Study on the Catalytic Reaction of Methionine Synthase VII. Synthesis of 5-Amino-6-methyluracil [J]. Chin. J. Org. Chem., 2003, 23(10): 1111-1113.
[4]	Liu Junyi;Ma Xiaoyan. Study on synthesis of ethyl 3-Oxo-(S)-(+)-6,7-di-O- idsopropylidene- 6,7-dihydroxyheptanoate [J]. Chin. J. Org. Chem., 2001, 21(1): 71-74.
[5]	XIAO YAN;GU LIANQUAN;XU JIANXING. Synthesis of azidosalicylamides: A new molecular probe of mitochondrial oxido-reductase inhibitor type [J]. Chin. J. Org. Chem., 1997, 17(4): 354-358.