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Synthesis 2022; 54(06): 1621-1632
DOI: 10.1055/a-1677-4881
DOI: 10.1055/a-1677-4881
paper
An Oxidant- and Catalyst-Free Synthesis of Dibenzo[a,c]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1H-indoles
We are grateful for financial support from the National Natural Science Foundation of China (No. 21672132).
Abstract
An efficient methodology for the synthesis of dibenzo[a,c]carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λ = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles.
Key words
photocyclization - 2,3-diphenyl-1H-indoles - hydrogen evolution - [1,5]-H shift - dibenzo[a,c]carbazolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1677-4881.
- Supporting Information
Publication History
Received: 02 September 2021
Accepted after revision: 23 October 2021
Accepted Manuscript online:
23 October 2021
Article published online:
30 November 2021
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References
- 1 Conchon E, Anizon F, Aboab B, Prudhomme M. J. Med. Chem. 2007; 50: 4669
- 2 Gu W, Qiao C, Wang S.-F, Hao Y, Miao T.-T. Bioorg. Med. Chem. Lett. 2014; 24: 328
- 3 Wang Y.-Q, Li X.-H, He Q, Chen Y, Xie Y.-Y, Ding J, Miao Z.-H, Yang C.-H. Eur. J. Med. Chem. 2011; 46: 5878
- 4 Gu W, Wang S. Eur. J. Med. Chem. 2010; 45: 4692
- 5 Xiao L, Chen Z, Qu B, Luo J, Kong S, Gong Q, Kido J. Adv. Mater. 2011; 23: 926
- 6 Aizawa N, Pu Y.-J, Chiba T, Kawata S, Sasabe H, Kido J. Adv. Mater. 2014; 26: 7543
- 7 Blouin N, Michaud A, Leclerc M. Adv. Mater. 2007; 19: 2295
- 8 Wu Y, Peng X, Luo B, Wu F, Liu B, Song F, Huang P, Wen S. Org. Biomol. Chem. 2014; 12: 9777
- 9 Guo S, Liu Y, Zhao L, Zhang X, Fan X. Org. Lett. 2019; 21: 6437
- 10 Cai J, Wu B, Rong G, Zhang C, Qiu L, Xu X. Org. Lett. 2018; 20: 2733
- 11 Mudry CA, Frasca AR. Tetrahedron 1974; 30: 2983
- 12 Mallory FB, Butler KE, Bérubé A, Luzik ED, Mallory CW, Brondyke EJ, Hiremath R, Ngo P, Carroll PJ. Tetrahedron 2001; 57: 3715
- 13 Jørgensen KB. Molecules 2010; 15: 4334
- 14 Tsukamoto T, Dong G. Angew. Chem. Int. Ed. 2020; 59: 15249
- 15 Park Y.-T, Jung C.-H, Kim M.-S, Kim K.-W, Song NW, Kim D. J. Org. Chem. 2001; 66: 2197
- 16 Kang Y, Wang T, Liang Y, Zhang Y, Wang R, Zhang Z. RSC Adv. 2017; 7: 44333
- 17 Han J, Wang T, Liang Y, Li Y, Li C, Wang R, Feng S, Zhang Z. Org. Lett. 2017; 19: 3552
- 18a Zhang W, Wang P, Zhang X, Wang R, Wang T, Liu Z, Zhang Z. Chin. J. Chem. 2021; 39: 2213
- 18b Fan J, Zhang W, Gao W, Wang T, Duan W.-L, Liang Y, Zhang Z. Org. Lett. 2019; 21: 9183
- 19 Houck HA, De Bruycker K, Barner-Kowollik C, Winne JM, Du Prez FE. Macromolecules 2018; 51: 3156
- 20 Irie M, Fukaminato T, Matsuda K, Kobatake S. Chem. Rev. 2014; 114: 12174
- 21 Hoffmann R, Woodward RB. Acc. Chem. Res. 1968; 1: 17
- 22 Shi Y.-g, Mellerup SK, Yuan K, Hu G.-F, Sauriol F, Peng T, Wang N, Chen P, Wang S. Chem. Sci. 2018; 9: 3844
- 23 Yu J.-W, Mao S, Wang Y.-Q. Tetrahedron Lett. 2015; 56: 1575
- 24 Chen X, Chen Z, So CM. J. Org. Chem. 2019; 84: 6337
- 25 Fu Y, Yang Y, Hügel HM, Du Z, Wang K, Huang D, Hu Y. Org. Biomol. Chem. 2013; 11: 4429
- 26 Mathew P, Mathew D, Asokan CV. Synth. Commun. 2007; 37: 661
- 27 Arisawa M, Kuwajima M, Toriyama F, Li G, Yamaguchi M. Org. Lett. 2012; 14: 3804
- 28 Takise R, Muto K, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2014; 53: 6791
- 29 Shu B, Wang X.-T, Shen Z.-X, Che T, Zhong M, Song J.-L, Kang H.-J, Xie H, Zhang L, Zhang S.-S. Org. Chem. Front. 2020; 7: 1802
- 30 Chen HY, Kim S, Wu JY, Birzin ET, Chan W, Yang YT, Dahllund J, DiNinno F, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg. Med. Chem. Lett. 2004; 14: 2551
- 31 Wommack AJ, Moebius DC, Travis AL, Kingsbury JS. Org. Lett. 2009; 11: 3202
- 32 Houck HA, De Bruycker K, Billiet S, Dhanis B, Goossens H, Catak S, Van Speybroeck V, Winne JM, Du Prez FE. Chem. Sci. 2017; 8: 3098
- 33 He P, Du Y, Liu G, Cao C, Shi Y, Zhang J, Pang G. RSC Adv. 2013; 3: 18345
- 34 Yan H, Wang H, Li X, Xin X, Wang C, Wan B. Angew. Chem. Int. Ed. 2015; 54: 10613
- 35 Zhao D, Shi Z, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 12426
- 36 Cacchi S, Fabrizi G, Goggiamani A, Perboni A, Sferrazza A, Stabile P. Org. Lett. 2010; 12: 3279
- 37 Algul O, Kaessler A, Apcin Y, Yilmaz A, Jose J. Molecules 2008; 13: 736
- 38 San Jang S, Kim YH, Youn SW. Org. Lett. 2020; 22: 9151
- 39 Lu C, Huang H, Tuo X, Jiang P, Zhang F, Deng G.-J. Org. Chem. Front. 2019; 6: 2738
- 40 Han J.-S, Chen S.-Q, Zhong P, Zhang X.-H. Synth. Commun. 2014; 44: 3148
- 41 Bhunia SK, Polley A, Natarajan R, Jana R. Chem. Eur. J. 2015; 21: 16786
- 42 Szmuszkovicz J. Org. Prep. Proced. 1969; 1: 105
- 43 Yang Y, Zhou B, Zhu X, Deng G, Liang Y, Yang Y. Org. Lett. 2018; 20: 5402