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DOI: 10.1055/a-2547-6153
One-Pot Synthesis of Benzo[g]indazoles via Suzuki–Miyaura Coupling and Aldol Condensation Cascade Reaction
Authors
This research was supported by the Korea Research Institute of Chemical Technology (KRICT, KN2431-10) and the Bio & Medical Technology Development Program of the National Research Foundation (NRF) funded by the Korean government (MSIT) (NRF-RS-2023-00235550).
Abstract
A highly efficient one-pot synthesis of benzo[g]indazole derivatives has been achieved through a cascade Suzuki–Miyaura coupling and aldol condensation reaction. Using Pd(OAc)2 and S-Phos as the catalytic system, the reaction delivered excellent yields and showed broad tolerance for various substituents on 2-formylphenylboronic acids. Moreover, this method was successfully applied to the synthesis of benzo[g]indazole-5-carbonitrile and pyrazolo[4,3-h]quinoline-5-carbonitrile derivatives by altering the coupling partners. This versatile protocol offers a straightforward and effective method for synthesizing biologically significant heterocyclic compounds.
Key words
benzo[g]indazoles - Suzuki–Miyaura coupling - aldol condensation - one-pot reaction - 2-formylphenylboronic acids - pyrazolo[4,3-h]quinolineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2547-6153.
- Supporting Information (PDF)
Publication History
Received: 06 January 2025
Accepted after revision: 27 February 2025
Accepted Manuscript online:
27 February 2025
Article published online:
25 March 2025
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References
- 1a Mal S, Malik U, Mahapatra M, Mishra A, Pal D, Paidesetty SK. Drug Dev. Res. 2022; 83: 1469
- 1b Puri S, Sawant S, Juvale K. J. Mol. Struct. 2023; 1284: 135327
- 2a Kim J, Joo JM. Bull. Korean Chem. Soc. 2022; 43: 1173
- 2b Müller S, Lee W, Song JY, Kang E, Joo JM. Chem. Commun. 2022; 58: 10809
- 2c Kim HT, Kang E, Kim M, Joo JM. Org. Lett. 2021; 23: 3657
- 3 Ohno H, Minamiguchi D, Nakamura S, Shu K, Okazaki S, Honda M, Misu R, Moriwaki H, Nakanishi S, Oishi S, Kinoshita T, Nakanishi I, Fujii N. Bioorg. Med. Chem. 2016; 24: 1136
- 4a Murineddu G, Ruiu S, Mussinu JM, Loriga G, Grella GE, Carai MA. M, Lazzari P, Pani L, Pinna GA. Bioorg. Med. Chem. 2005; 13: 3309
- 4b Deiana V, Gómez-Cañas M, Pazos MR, Fernández-Ruiz J, Asproni B, Cichero E, Fossa P, Muñoz E, Deligia F, Murineddu G, García-Arencibia M, Pinna GA. Eur. J. Med. Chem. 2016; 112: 66
- 5 Shen HC, Ding F.-X, Deng Q, Wilsie LC, Krsmanovic ML, Taggart AK, Carballo-Jane E, Ren N, Cai T.-Q, Wu T.-J, Wu KK, Cheng K, Chen Q, Wolff MS, Tong X, Holt TG, Waters MG, Hammond ML, Tata JR, Colletti SL. J. Med. Chem. 2009; 52: 2587
- 6 Suzuki Y, Oishi S, Takei Y, Yasue M, Misu R, Naoe S, Hou Z, Kure T, Nakanishi I, Ohno H, Hirasawa A, Tsujimoto G, Fujii N. Org. Biomol. Chem. 2012; 10: 4907
- 7a Kim YH, Lee H, Kim YJ, Kim BT, Heo J.-N. J. Org. Chem. 2008; 73: 495
- 7b Choi YL, Kim BT, Heo J.-N. J. Org. Chem. 2012; 77: 8762
- 8 Kim JK, Kim YH, Nam HT, Kim BT, Heo J.-N. Org. Lett. 2008; 10: 3543
- 9 Park K.-Y, Kim BT, Heo J.-N. Eur. J. Org. Chem. 2014; 164
- 10 Choi YL, Yu C.-M, Kim BT, Heo J.-N. J. Org. Chem. 2009; 74: 3948
- 11a Fandrick DR, Sanyal S, Kaloko J, Mulder JA, Wang Y, Wu L, Lee H, Roschangar F, Hoffmann M, Senanayake CH. Org. Lett. 2015; 17: 2964
- 11b Ostache N.-C, Hiebel M.-A, Fînaru A.-L, Allouchi H, Guillaumet G, Suzenet F. RSC Adv. 2021; 11: 9756
- 12a Yuan D, Huynh HV. Molecules 2012; 17: 2491
- 12b Willis MC, Taylor D, Gillmore AT. Tetrahedron 2006; 62: 11513
- 12c Choi YL, Lee H, Kim BT, Choi K, Heo J.-N. Adv. Synth. Catal. 2010; 352: 2041
- 13 Jeon AR, Kim ME, Park JK, Shin WK, An DK. Tetrahedron 2014; 70: 4420
- 14 Huang Q, Tran G, Gomez Pardo D, Tsuchiya T, Hillebrand S, Vors J.-P, Cossy J. Tetrahedron 2015; 71: 7250
- 15 Martin N, Pierre C, Davi M, Jazzar R, Baudoin O. Chem. Eur. J. 2012; 18: 4480
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