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Synthesis 2024; 56(22): 3512-3518
DOI: 10.1055/a-2378-4540
DOI: 10.1055/a-2378-4540
paper
Solvent-Controlled Divergent Synthesis of Thiocyanated Carbazoles and Di/Triphenylamines
This research was supported by Zhejiang Provincial Natural Science Foundation of China (Grant No. LY23B040001) and Programs Supported by Ningbo Natural Science Foundation (Grant No. 202003N4009).
Abstract
A solvent-controlled divergent thiocyanation of carbazoles and di/triphenylamines has been developed. Using either CH3CN/H2O (3:1) or DMSO as the solvent, a facile and efficient protocol for the solvent-controlled divergent synthesis of mono- and di-thiocyanation of carbazoles and di/triphenylamines was achieved. The salient features of this transformation include simple and mild reaction conditions, easily available substrates, and broad substrate scope.
Key words
thiocyanation - carbazoles - di/triphenylamines - divergent synthesis - solvent-controlledSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2378-4540.
- Supporting Information
Publication History
Received: 30 June 2024
Accepted after revision: 01 August 2024
Accepted Manuscript online:
01 August 2024
Article published online:
26 August 2024
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References
- 1 Lee C. -F. Liu Y.-C., Badsara S. S Chem. Asian J.; 2014, 9: 706
- 2a Suzuki H, Kawakami S, Ohsawa N, Seo S. Patent EP 2166001 A1, 2010
- 2b Chen D-J, Xu X-Y, Shao L, Li Z, Dong X-J, Hou S, Zhang J-L, Wang R. Patent CN 107625766 A, 2018
- 2c Kokorekin VA, Terent’ev AO, Ramenskaya GV, Grammatikova N.É, Rodionova GM, Ilovaiskii AI. Pharm. Chem. J. 2013; 47: 422
- 3 Riemschneider R, Wojahn F, Orlick G. J. Am. Chem. Soc. 1951; 73: 5905
- 4 Segalovich-Gerendash G, Rozenberg I, Alassad N, Nechmad NB, Goldberg I, Kozuch S, Lemcoff NG. ACS Catal. 2020; 10: 4827
- 5 Zhang T, Deng G, Li H, Liu B, Tan Q, Xu B. Org. Lett. 2018; 20: 5439
- 6 Chen J, Wang T, Wang T, Lin A, Yao H, Xu J. Org. Chem. Front 2017; 4: 130
- 7 Prabhu KR, Ramesha AR, Chandrasekaran S. J. Org. Chem. 1995; 60: 7142
- 8a Li C, Long P, Wu H, Yin H, Chen F.-X. Org. Biomol. Chem. 2019; 17: 7131
- 8b de Oliveira Lima Filho E, Malvestiti I. ACS Omega 2020; 5: 33329
- 9 Rezayati S, Ramazani A. Tetrahedron 2020; 76: 131382
- 10a Huang W, Gao Z, Zhang Z, Fang W, Wang Z, Wan Z, Shi L, Wang K, Ke S. Bioorg. Chem. 2021; 113: 104991
- 10b Kumar N, Lal N, Nemaysh V, Luthra PM. Bioorg. Chem. 2020; 100: 103911
- 10c Teja PK, Patel P, Bhavsar D, Bindusri C, Jadhav K, Chauthe SK. Phytochemistry 2021; 190: 112865
- 11 Makarov AS, Bakiev AN, Eshmemeteva DA. Org. Chem. Front. 2023; 10: 2760
- 12a Chakrabarty M, Sarkar S. Tetrahedron Lett. 2003; 44: 8131
- 12b Nikoofar K, Gorji S. J. Sulfur Chem. 2015; 36: 178
- 13a Khalili D. Chin. Chem. Lett. 2015; 26: 547
- 13b Mete TB, Khopade TM, Bhat RG. Tetrahedron Lett. 2017; 58: 415
- 14 Pan X.-Q, Lei M.-Y, Zou J.-P, Zhang W. Tetrahedron Lett. 2009; 50: 347
- 15 Hosseini-Sarvari M, Hosseinpour Z, Koohgard M. New J. Chem. 2018; 42: 19237
- 16 Zhang Y, Gao H, Guo J, Zhang H, Yao X. Chem. Commun. 2021; 57: 13166
- 17a Xiao E.-K, Wu X.-T, Ma F, Feng X, Chen P, Jiang Y.-J. Org. Lett. 2021; 23: 449
- 17b Wu X.-T, Xiao E.-K, Ma F, Yin J, Wang J, Chen P, Jiang Y.-J. J. Org. Chem. 2021; 86: 6734
- 17c Xiao E.-K, Wu X.-T, Ma F, Miao L.-W, Jiang Y.-J, Chen P. Chem. Commun. 2021; 57: 7148
- 17d Yin J, Chen P, Miao L.-W, Wang J, Jiang Y.-J. Eur. J. Org. Chem. 2023; e202300290
- 18a Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal. 2018; 8: 5085
- 18b Yang H, Duan X.-H, Zhao J.-F, Guo L.-N. Org. Lett. 2015; 17: 1998
- 19 Zhang P, Yin Y, Wang Z, Yu C, Zhu Y, Yan D, Liu W, Mai Y. Macromolecules 2021; 54: 3543