Visible-Light-Induced Three-Component Reactions of α-Diazoesters, Indazoles, and Cyclic Ethers

Abstract

An efficient method was developed for the construction of N-short-chain ether-attached carbonyl group-substituted indazoles. The visible-light-induced three-component reactions of α-diazoesters, indazoles, and cyclic ethers, under extremely mild conditions, led to the corresponding mixture of N ¹ and N ² short-chain ether-substituted indazoles in good to excellent yields.

Key words

visible-light catalysis - α-diazoester - indazole - cyclic ether - multicomponent reaction

Publication History

Received: 06 August 2024

Accepted after revision: 29 October 2024

Accepted Manuscript online:
29 October 2024

Article published online:
18 November 2024

• References


For selected reviews, see:
• 1a Yu X.-Y, Chen J.-R, Xiao W.-J. Chem. Rev. 2021; 121: 506
• 1b Wang X, Zhang Y, Sun K, Meng J, Zhang B. Chin. J. Org. Chem. 2021; 41: 4588
• 1c Yu X.-Y, Zhao Q.-Q, Chen J, Xiao W.-J, Chen J.-R. Acc. Chem. Res. 2020; 53: 1066
• 1d Xuan J, He X.-K, Xiao W.-J. Chem. Soc. Rev. 2020; 49: 2546
• 1e Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47: 7190
• 1f Gentry EC, Knowles RR. Acc. Chem. Res. 2016; 49: 1546
• 1g Chen J.-R, Hu X.-Q, Lu L.-Q, Xiao W.-J. Chem. Soc. Rev. 2016; 45: 2044
• 1h Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322

For selective recent reports, see:
• 2a Dong D.-Q, Li L.-X, Li G.-H, Deng Q, Wang Z.-L, Long S. Chin. J. Catal. 2019; 40: 1494
• 2b Liu X.-C, Sun K, Chen X.-L, Wang W.-F, Liu Y, Li Q.-L, Peng Y.-Y, Qu L.-B, Yu B. Adv. Synth. Catal. 2019; 361: 3712
• 2c Gan Z, Li G, Yang X, Yan Q, Xu G, Li G, Jiang Y.-Y, Yang D. Sci. China: Chem. 2020; 63: 1652
• 2d Xie L.-Y, Liu Y.-S, Ding H.-R, Gong S.-F, Tan J.-X, He J.-Y, Cao Z, He W.-M. Chin. J. Catal. 2020; 41: 1168
• 2e He W.-B, Gao L.-Q, Chen X.-J, Wu Z.-L, Huang Y, Cao Z, Xu X.-H, He W.-M. Chin. Chem. Lett. 2020; 31: 1895
• 2f Shi S, Wei W. Chin. J. Org. Chem. 2020; 40: 2170
• 2g Meng N, Lv Y, Liu Q, Liu R, Zhao X, Wei W. Chin. Chem. Lett. 2021; 32: 258
• 2h Wang Z, Liu Q, Liu R, Ji Z, Li Y, Zhao X, Wei W. Chin. Chem. Lett. 2022; 32: 1479

For reviews, see:
• 3a Xie Z.-Y, Xuan J. Chem. Commun. 2024; 60: 2125
• 3b Durka J, Turkowska J, Gryko D. ACS Sustainable Chem. Eng. 2021; 9: 8895
• 3c Yang Z, Stivanin ML, Jurberg ID, Koenigs RM. Chem. Soc. Rev. 2020; 49: 6833
• 3d Cai B.-G, Xuan J. Chin. J. Org. Chem. 2021; 41: 4565
• 3e Ciszewski LW, Rybicka-jasinska K, Gryko D. Org. Biomol. Chem. 2019; 17: 432
• 4a Silva AF, Afonso MA. S, Cormanich RA, Jurberg ID. Chem. Eur. J. 2020; 26: 5648
• 4b Xiao TB, Mei MJ, He YW, Zhou L. Chem. Commun. 2018; 54: 8865
• 5a Zhao B, Yang L, Cheng K, Zhou L, Wan J.-P. Chin. J. Org. Chem. 2021; 41: 4732
• 5b Cheng X, Cai B.-G, Mao H, Lu J, Li L, Wang K, Xuan J. Org. Lett. 2021; 23: 4109
• 5c Ye C, Cai B.-G, Lu J, Cheng X, Li L, Pan Z.-W, Xuan J. J. Org. Chem. 2021; 86: 1012
• 5d Hommelsheim R, Guo Y, Yang Z, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2019; 58: 1203
• 5e He F, Koenigs RM. Chem. Commun. 2019; 55: 4881
• 5f Jana S, Yang Z, Pei C, Xu X, Koenigs RM. Chem. Sci. 2019; 10: 10129
• 5g Guo Y, Nguyen TV, Königs RM. Org. Lett. 2019; 21: 8814
• 5h Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112

See, for instance:
• 6a Zhou S, Cai B, Hu C, Cheng X, Li L, Xuan J. Chin. Chem. Lett. 2021; 32: 2577
• 6b Jana S, Yang Z, Li F, Empel C, Ho J, Königs RM. Angew. Chem. Int. Ed. 2020; 59: 5562
• 6c Empel C, Jana S, Pei C, Nguyen TV, Königs RM. Org. Lett. 2020; 22: 7225
• 6d Yang J, Wang G, Zhou H, Li Z, Ma B, Song M, Sun R, Huo C. Org. Biomol. Chem. 2021; 19: 394

See, for instance:
• 7a Stivanin ML, Fernandes AA. G, Silva AF, Okada CY. Jr, Jurberg ID. Adv. Synth. Catal. 2020; 362: 1106
• 7b Okada CY. Jr, dos Santos CY, Jurberg ID. Tetrahedron 2020; 76: 131316
• 7c Yang J, Duan J, Wang G, Zhou H, Ma B, Wu C, Xiao J. Org. Lett. 2020; 22: 7284
• 7d Empel C, Patureau FW, Königs RM. J. Org. Chem. 2019; 84: 11316
• 8a Zhou H, Wang G, Wang C, Yang J. Org. Lett. 2022; 24: 1530
• 8b Liu R, Liu Q, Meng H, Ding H, Hao J, Ji Z, Yue H, Wei W. Org. Chem. Front. 2021; 8: 1970

See, for instance:
• 9a Gallo RD. C, Duarte M, da Silva AF, Okada CY. Jr, Deflon VM, Jurberg ID. Org. Lett. 2021; 23: 8916
• 9b Cai B.-G, Luo S.-S, Li L, Li L, Xuan J, Xiao W.-J. CCS Chem. 2020; 2: 2764
• 9c Yang Z, Guo Y, Königs RM. Chem. Eur. J. 2019; 25: 6703
• 9d Yang J, Wang J, Huang H, Qin G, Jiang Y, Xiao T. Org. Lett. 2019; 21: 2654

For selected reviews, see:
• 10a Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
• 10b Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
• 10c Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
• 10d de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
• 10e Ganeem B. Acc. Chem. Res. 2009; 42: 463
• 11 He F, Pei C, Königs RM. Chem. Commun. 2020; 56: 599
• 12a Li Q, Cai B.-G, Li L, Xuan J. Org. Lett. 2021; 23: 6951
• 12b Stivanin ML, Duarte M, Leão LP. M. O, Saito FA, Jurberg ID. J. Org. Chem. 2021; 86: 17528
• 13 Maiti D, Das R, Sen S. Green Chem. 2021; 23: 8533
• 14a Lv Y, Ding H, You J, Wei W, Yi D. Chin. Chem. Lett. 2024; 35: 109107
• 14b Cai B.-G, Li Q, Zhang Q, Li L, Xuan J. Org. Chem. Front. 2021; 8: 5982
• 15a Stivanin ML, Gallo RD. C, Spadeto JP. M, Cormanich RA, Jurberg ID. Org. Chem. Front. 2022; 9: 1321
• 15b Ding H, Wang Z, Qu C, Lv Y, Zhao X, We W. Org. Chem. Front. 2022; 9: 5530
• 16 Yang ZX, Wu X, Xiang CL, Yu J.-T, Pan CD. Asian J. Org. Chem. 2023; 12: e202300357
• 17 Wang Z, Meng N, Lv Y, Wei W, Yue H, Zhong G. Chin. Chem. Lett. 2023; 34: 107599
• 18a Prati F, Uliassi E, Bolognesi ML. Chem. Med. Chem. 2014; 5: 853
• 18b Bolognesi ML, Cavalli A. ChemMedChem. 2016; 11: 1190
• 18c Ivasiv V, Albertini C, Gonçalves AE, Rossi M, Bolognesi ML. Curr. Top. Med. Chem. 2019; 19: 1694
• 19 Kerru N, Singh P, Koorbanally N, Raj R, Kumar V. Eur. J. Med. Chem. 2017; 142: 179
• 20 Liu Y, Yang Q, Wang W, Fu Y, Ding QP, Peng YY. Org. Biomol. Chem. 2024; 22: 4332
• 21a Yuan T, Nahar P, Sharma M, Liu K, Slitt A, Aisa HA, Seeram NP. J. Nat. Prod. 2014; 77: 2316
• 21b Ali Z, Ferreira D, Carvalho P, Avery MA, Khan IA. J. Nat. Prod. 2008; 71: 1111
• 21c Atta-ur-Rahman, Malik S, Hasan SS, Choudhary MI, Ni C.-Z, Clardy J. Tetrahedron Lett. 1995; 36: 1993
• 21d Thangadurai A, Minu M, Wakode S, Agrawal S, Narasimhan B. Med. Chem. Res. 2011; 21: 1509
• 22 Cerecetto H, Gerpe A, González M, Arán VJ, de Ocáriz CO. Mini-Rev. Med. Chem. 2005; 5: 869
• 23a Harris PA, Boloor A, Cheung M, Kumar R, Crosby RM, Davis-Ward RG, Epperly AH, Hinkle KW, Hunter RN. III, Johnson JH, Knick VB, Laudeman CP, Luttrell DK, Mook RA, Nolte RT, Rudolph SK, Szewczyk JR, Truesdale AT, Veal JM, Wang L, Stafford JA. J. Med. Chem. 2008; 51: 4632
• 23b Jones P, Altamura S, Boueres J, Ferrigno F, Fonsi M, Giomini C, Lamartina S, Monteagudo E, Ontoria JM, Orsale MV, Palumbi MC, Pesci S, Roscilli G, Scarpelli R, Schultz-Fademrecht C, Toniatti C, Rowley M. J. Med. Chem. 2009; 52: 7170
• 23c Chung CK, Bulger PG, Kosjek B, Belyk KM, Rivera N, Scott ME, Humphrey GR, Limanto J, Bachert DC, Emerson KM. Org. Process Res. Dev. 2014; 18: 215
• 23d Schmidt D, Rodat T, Heintze L, Weber J, Horbert R, Girreser U, Raeker T, Bußmann L, Kriegs M, Harke B, Peifer C. ChemMedChem. 2018; 13: 2415
• 24a Cheung M, Boloor A, Stafford JA. J. Org. Chem. 2003; 68: 4093
• 24b Hunt KW, Moreno DA, Suiter N, Clark CT, Kim G. Org. Lett. 2009; 11: 5054
• 24c Ge D, Zhang X, Chen S, Pu L, Yu X. Tetrahedron Lett. 2015; 56: 4811
• 24d He H, Yan J, Jin ZJ, Yan Z, Yan Q, Wang W, Jiang H, Wang H, Chen F. Chem. Commun. 2022; 58: 6429
• 25a Liang JZ, Huang J, Yang Q, Fu Y, Ding QP, Peng YY. Green Chem. 2022; 24: 8441
• 25b Zhang ZP, Jiang X, Deng ZH, Wang H, Huang J, Peng YY. RSC Adv. 2017; 7: 27603
• 26 Huang J, Fu Y, Deng ZH, Chen W, Song ZB, Peng YY. Org. Biomol. Chem. 2020; 18: 9863
• 27 Li P, Zhao JJ, Wu CR, Larock RC, Shi F. Org. Lett. 2011; 13: 3340
• 28a Yi XY, Zhang ZP, Huang H, Baell JB, Yu Y, Huang F. Chin. J. Org. Chem. 2019; 39: 544
• 28b Keipour H, Ollevier T. Org. Lett. 2017; 19: 5736