Synthesis, Table of Contents Synthesis 2024; 56(24): 3889-3902DOI: 10.1055/a-2457-0146 paper Visible-Light-Induced Three-Component Reactions of α-Diazoesters, Indazoles, and Cyclic Ethers Authors Author Affiliations Wei Wang‡ a College of Chemistry & Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Yan Liu‡ a College of Chemistry & Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Qin Yang b College of Life Science, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Yang Fu∗ a College of Chemistry & Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Qiuping Ding a College of Chemistry & Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Yiyuan Peng ∗ a College of Chemistry & Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. China Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) 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 Key wordsvisible-light catalysis - α-diazoester - indazole - cyclic ether - multicomponent reaction Full Text References 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 Supplementary Material Supplementary Material Supporting Information (PDF)
