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Triton-B Catalyzed, Green and Efficient Method for the Synthesis of Dithiocarbazates
Corresponding Author(s) : Sadaf Zaidi
Asian Journal of Chemistry,
Vol. 31 No. 7 (2019): Vol 31 Issue 7
Abstract
A novel, solvent free and high yielding method was accomplished for one-pot synthesis of dithiocarbazates by the reaction of various alkyl halides (primary, secondary and tertiary) with variety of substituted hydrazines using Triton-B (benzyl-trimethylammonium hydroxide) and carbon di sulphide. This new method of synthesizing dithiocarbazates involves mild conditions, simple procedures and high yields of the products as compared to previously used methods.
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- U. Ragnarsson, Chem. Soc. Rev., 30, 205 (2001); https://doi.org/10.1039/b010091a.
- B. Mishra, S. Reiling, D. Zarena and G. Wang, Curr. Opin. Chem. Biol., 38, 87 (2017); https://doi.org/10.1016/j.cbpa.2017.03.014.
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- E.U. Schmidt, Hydrazine and its Derivatives Preparation, Properties, Applications, Wiley-Interscience: New York, edn 2 (2001).
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- S.-N. Li, Q.-G. Zhai, M.-C. Hu and Y.-C. Jiang, J. Chem. Crystallogr., 41, 12 (2011); https://doi.org/10.1007/s10870-010-9825-4.
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- A. Monaci and F. Trali, J. Chem. Soc. Dalton Trans., 499 (1980); https://doi.org/10.1039/DT9800000499.
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- M.A. Ali and S.E. Livingstone, Coord. Chem. Rev., 13, 101 (1974); https://doi.org/10.1016/S0010-8545(00)80253-2.
- M.R. Maurya, S.S. Khurana, A. Azam, W. Zhang and D. Rheder, Eur. J. Inorg. Chem., 2003, 1966 (2003); https://doi.org/10.1002/ejic.200200642.
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References
U. Ragnarsson, Chem. Soc. Rev., 30, 205 (2001); https://doi.org/10.1039/b010091a.
B. Mishra, S. Reiling, D. Zarena and G. Wang, Curr. Opin. Chem. Biol., 38, 87 (2017); https://doi.org/10.1016/j.cbpa.2017.03.014.
F.R. Pavan, P.L. da S. Maia, S.R. Leite, V.M. Deflon, A.A. Batista, D.N. Sato, S.G. Franzblau and C.Q. Leite, Eur. J. Med. Chem., 45, 1898 (2010); https://doi.org/10.1016/j.ejmech.2010.01.028.
H. van der Goot, Eur. J. Chem., 35, 5 (2000); https://doi.org/10.1016/S0223-5234(00)00101-X.
E.U. Schmidt, Hydrazine and its Derivatives Preparation, Properties, Applications, Wiley-Interscience: New York, edn 2 (2001).
S. Kubota, M. Uda, Y. Mori, F. Kametani and H. Terada, J. Med. Chem., 21, 591 (1978); https://doi.org/10.1021/jm00204a018.
M.S.C. Pedras and M. Jha, Bioorg. Med. Chem., 14, 4958 (2006); https://doi.org/10.1016/j.bmc.2006.03.014.
N. Bharti, M.R. Maurya, F. Naqvi and A. Azam, Bioorg. Med. Chem. Lett., 10, 2243 (2000); https://doi.org/10.1016/S0960-894X(00)00446-7.
B. Neelam, M. Mannar R, N. Fehmida, B. Alok, B. Sudha and A. Amir, Eur. J. Med. Chem., 35, 481 (2000); https://doi.org/10.1016/S0223-5234(00)00145-8.
H.S. Chen, Z.H. Li, Y.H. Han and Z.W. Wang, Chin. Chem. Lett., 10, 365 (1999).
T.J. Connolly, A.J. Crittall, A.S. Ebrahim and G. Ji, Org. Process Res. Dev., 4, 526 (2000); https://doi.org/10.1021/op0002904.
M.J. Hauser, J. Org. Chem., 31, 968 (1966); https://doi.org/10.1021/jo01341a514.
V. del Amo, A.P. McGlone, C. Foster and A.P. Davis, J. Comb. Chem., 7, 1 (2005); https://doi.org/10.1021/cc049875q.
M.T.H. Tarafder, M.A. Ali, N. Saravanan, W.Y. Weng, S. Kumar, N. Umar-Tsafe and K.A. Crouse, Transition Met. Chem., 25, 3 (2000); https://doi.org/10.1023/A:1007044910814.
S.-N. Li, Q.-G. Zhai, M.-C. Hu and Y.-C. Jiang, J. Chem. Crystallogr., 41, 12 (2011); https://doi.org/10.1007/s10870-010-9825-4.
F.N.-F. How, K.A. Crouse, M.I.M. Tahir, M.T.H. Tarafder and A.R. Cowley, Polyhedron, 27, 3325 (2008); https://doi.org/10.1016/j.poly.2008.07.022.
M. Quibell, W.G. Turnell and T. Johnson, J. Chem. Soc. Perkin Trans. I, 22, 2843 (1993); https://doi.org/10.1039/p19930002843.
C.J. Gray, M. Quibell, N. Baggett and T. Hammerle, Int. J. Pept. Protein Res., 40, 351 (1992); https://doi.org/10.1111/j.1399-3011.1992.tb00311.x.
X. Huang, E. Tang, W.-M. Xu and J. Cao, J. Comb. Chem., 7, 802 (2005); https://doi.org/10.1021/cc0498231.
J.Y. Hwang, H.S. Choi, D.H. Lee and Y.D. Gong, J. Comb. Chem., 7, 816 (2005); https://doi.org/10.1021/cc0500957.
A. Monaci and F. Trali, J. Chem. Soc. Dalton Trans., 499 (1980); https://doi.org/10.1039/DT9800000499.
S.B. Kalia, V. Sharma, K. Lumba, G. Kaushal and A. Sharma, Indian J. Pharm. Sci., 69, 438 (2007); https://doi.org/10.4103/0250-474X.34558.
M.A. Ali and S.E. Livingstone, Coord. Chem. Rev., 13, 101 (1974); https://doi.org/10.1016/S0010-8545(00)80253-2.
M.R. Maurya, S.S. Khurana, A. Azam, W. Zhang and D. Rheder, Eur. J. Inorg. Chem., 2003, 1966 (2003); https://doi.org/10.1002/ejic.200200642.
A. Saxena, J.K. Koacher and J.P.J. Tandon, Antibact. Antifung. Agent, 9, 435 (1981).
C. Bolzati, E. Benini, M. Cavazza-Ceccato, E. Cazzola, E. Malagò, S. Agostini, F. Tisato, F. Refosco and G. Bandoli, Bioconjug. Chem., 17, 419 (2006); https://doi.org/10.1021/bc050358q.
M.A. Ali, A.H. Mirza, R.J. Butcher and K.A. Crouse, Transition Met. Chem., 31, 79 (2006); https://doi.org/10.1007/s11243-005-6305-3.
H. Dyker, J. Scherkenbeck, D. Gondol, A. Goehrt and A. Harder, J. Org. Chem., 66, 3760 (2001); https://doi.org/10.1021/jo001749v.
S. Nara, T. Sakamoto, E. Miyazawa and Y. Kikugawa, Synth. Commun., 33, 87 (2003); https://doi.org/10.1081/SCC-120015563.
D.L. Fox, J.T. Ruxer, J.M. Oliver, K.L. Alford and R.N. Salvatore, Tetrahedron Lett., 45, 401 (2004); https://doi.org/10.1016/j.tetlet.2003.10.144.