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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

One-Pot Green Synthesis of Some Novel N-Substituted 5-Amino-1,3,4- Thiadiazole Derivatives

Author(s): Azizollah Habibi *, Sahar Khosravi , Seyyed M. Shahcheragh and Mohd B. Abdul Rahman

Volume 17, Issue 7, 2020

Page: [517 - 522] Pages: 6

DOI: 10.2174/1570178616666190926105533

Price: $65

Abstract

In the current study, a green, one-pot, three-component reaction was performed to prepare novel N-substituted 5-amino-1,3,4-thiadiazole derivatives. The thiadiazoles were obtained from the reaction of a ketene S,S-acetal of Meldrum’s acid or barbituric acid (as key intermediates), hydrazine, and isothiocyanate. The key advantages of this manner include environmentally safe reactions, high yield, appropriate reaction time, simple reaction conditions, and use of a green reaction solvent. The structure of thiadiazoles was determined based on the spectroscopic data.

Keywords: 5-amino-1, 3, 4-thiadiazole, Thiosemicarbazide, Ketene S, S-acetal, Meldrum’s acid, Barbituric acid, Deep Eutectic Solvents.

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[1]
(a) Reactions in Water, 1st ed; Li, C-J. Green SolventsWiley-VCH: Weinheim, 2011, p. 5.
(b) Arends, I.; Sheldon, R.; Hanefeld, U. Green Chemistry and Catalysis, 1st ed; Wiley-VCH: Weinheim, 2007.
[2]
(a) Katritzky, A.R. Handbook of Heterocyclic Chemistry; Pergamon Press: New York, 1985.
(b) Usol’tseva, S.V.; Andronnikova, G.P.; Mokrushi, V.S. Chem. Heterocycl. Compd., 1991, 27, 343.
[http://dx.doi.org/10.1007/BF00480827]
(c) Arora, P.; Arora, V.; Lamba, H.S.; Wadhwa, D. Int. J. Pharm. Sci. Res., 2012, 3, 2947.
(d) Hu, Y.; Li, C-Y.; Wang, X-M.; Yang, Y-H.; Zhu, H-L. Chem. Rev., 2014, 114(10), 5572-5610.
[http://dx.doi.org/10.1021/cr400131u] [PMID: 24716666]
[3]
(a) Gong, Y-D.; Lee, T. J. Comb. Chem., 2010, 12(4), 393-409.
[http://dx.doi.org/10.1021/cc100049u] [PMID: 20533849]
(b) Ahmad, T.; Sngh, A.K.; Jaiswal, N.; Singh, D. Inter. Res. J. Pharm., 2012, 3, 70.
[4]
Almajan, G.L.; Barbuceanu, S-F.; Bancescu, G.; Saramet, I.; Saramet, G.; Draghici, C. Eur. J. Med. Chem., 2010, 45(12), 6139-6146.
[http://dx.doi.org/10.1016/j.ejmech.2010.10.007] [PMID: 21036422]
[5]
Serban, G.; Stanasel, O.; Serban, E.; Bota, S. Drug Des. Devel. Ther., 2018, 12, 1545-1566.
[http://dx.doi.org/10.2147/DDDT.S155958] [PMID: 29910602]
[6]
Farghaly, T.A.; Abdallah, M.A.; Muhammad, Z.A. Molecules, 2011, 16(12), 10420-10432.
[http://dx.doi.org/10.3390/molecules161210420] [PMID: 22173335]
[7]
Foroumadi, A.; Kiani, Z.; Soltani, F. Farmaco, 2003, 58(11), 1073-1076.
[http://dx.doi.org/10.1016/S0014-827X(03)00158-7] [PMID: 14572857]
[8]
(a) Salgin-Gökşen, U.; Gökhan-Kelekçi, N.; Göktaş, O.; Köysal, Y.; Kiliç, E.; Işik, S.; Aktay, G.; Ozalp, M. Bioorg. Med. Chem., 2007, 15(17), 5738-5751.
[http://dx.doi.org/10.1016/j.bmc.2007.06.006] [PMID: 17587585]
(b) Mathew, V.; Keshavayya, J.; Vaidya, V.P.; Giles, D. Eur. Med. Chem., 2007, 42, 823.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.010]
[9]
Farghaly, T.A.; Abdallah, M.A.; Masaret, G.S.; Muhammad, Z.A. Eur. J. Med. Chem., 2015, 97, 320-333.
[http://dx.doi.org/10.1016/j.ejmech.2015.05.009]] [PMID: 26055810]
[10]
(a) Noolvi, M.N.; Patel, H.M.; Singh, N.; Gadad, A.K.; Cameotra, S.S.; Badiger, A. Eur. J. Med. Chem., 2011, 46(9), 4411-4418.
[http://dx.doi.org/10.1016/j.ejmech.2011.07.012]] [PMID: 21820217]
(b) Matysiak, J. Eur. J. Med. Chem., 2007, 42(7), 940-947.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.033] [PMID: 17320247]
[11]
Chen, C.J.; Song, B.A.; Yang, S.; Xu, G.F.; Bhadury, P.S.; Jin, L.H.; Hu, D.Y.; Li, Q.Z.; Liu, F.; Xue, W.; Lu, P.; Chen, Z. Chen. Bioorg. Med. Chem., 2007, 15, 3981.
[http://dx.doi.org/10.1016/j.bmc.2007.04.014] [PMID: 17452108]
[12]
Matysiak, J.; Skrzypek, A.; Niewiadomy, A. Heteroatom Chem., 2010, 21, 533.
[http://dx.doi.org/10.1002/hc.20645]
[13]
(a) Jatav, V.; Mishra, P.; Kashaw, S.; Stables, J.P. CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones. Eur. J. Med. Chem., 2008, 43(9), 1945-1954.
[http://dx.doi.org/10.1016/j.ejmech.2007.12.003] [PMID: 18222569]
(b) Pocar, F.C.D. J. Med. Chem., 44, 931.
[14]
(a) Khan, I.; Ali, S.; Hameed, S.; Rama, N.H.; Hussain, M.T.; Wadood, A.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Ali, S.; Choudhary, M.I. Eur. J. Med. Chem., 2010, 45(11), 5200-5207.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.034] [PMID: 20828889]
(b) Cressier, D.; Prouillac, C.; Hernandez, P.; Amourette, C.; Diserbo, M.; Lion, C.; Rima, G. Bioorg. Med. Chem., 2009, 17(14), 5275-5284.
[http://dx.doi.org/10.1016/j.bmc.2009.05.039] [PMID: 19502068]
[15]
Matysiak, J. Chem. Pharm. Bull. (Tokyo), 2006, 54(7), 988-991.
[http://dx.doi.org/10.1248/cpb.54.988] [PMID: 16819217]
[16]
(a) Farghaly, T.A.; Abdallah, M.A.; Masaret, G.S.; Muhammad, Z.A. Eur. J. Med. Chem., 2015, 97, 320-333.
[http://dx.doi.org/10.1016/j.ejmech.2015.05.009] [PMID: 26055810]
(b) Carvalho, S.A.; da Silva, E.F.; Santa-Rita, R.M.; de Castro, S.L.; Fraga, C.A.M. Bioorg. Med. Chem. Lett., 2004, 14(24), 5967-5970.
[http://dx.doi.org/10.1016/j.bmcl.2004.10.007] [PMID: 15546709]
(c) Sun, J.; Yang, Y.S.; Li, W.; Zhang, Y.B.; Wang, X.L.; Tang, J.F.; Zhu, H.L. Bioorg. Med. Chem. Lett., 2011, 21(20), 6116-6121.
[http://dx.doi.org/10.1016/j.bmcl.2011.08.039] [PMID: 21889345]
[17]
Sayed, A.R. Tetrahedron Lett., 2010, 51, 4490.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.060]
[18]
Shawali, A.S.; Párkanyi, C. J. Heterocycl. Chem., 1980, 17, 833.
[http://dx.doi.org/10.1002/jhet.5570170501]
[19]
(a) Hwang, J.Y.; Choi, H.S.; Lee, D.H.; Gong, Y.D. J. Comb. Chem., 2005, 7(6), 816-819.
[http://dx.doi.org/10.1021/cc0500957] [PMID: 16283790]
(b) Gong, Y.D.; Lee, T. J. Comb. Chem., 2010, 12(4), 393-409.
[http://dx.doi.org/10.1021/cc100049u] [PMID: 20533849]
[20]
(a) Kiryanov, A.A.; Sampson, P.; Seed, A.J. J. Org. Chem., 2001, 66(23), 7925-7929.
[http://dx.doi.org/10.1021/jo016063x] [PMID: 11701063]
(b) Polshettiwar, V.; Varma, R.S. Tetrahedron Lett., 2008, 49, 879.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.165]
[21]
Epishina, M.A.; Kulikov, A.S.; Ignat’ev, N.V.; Schulte, M.; Makhova, N.N. Mendeleev Commun., 2011, 21, 331.
[http://dx.doi.org/10.1016/j.mencom.2011.11.013]
[22]
(a) Gong, Y.D.; Lee, T. J. Comb. Chem., 2010, 12(4), 393-409.
[http://dx.doi.org/10.1021/cc100049u] [PMID: 20533849]
(b) Polshettiwar, V.; Varma, R.S. Tetrahedron Lett., 2008, 49, 879.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.165]
[23]
Shawali, A.S. J. Adv. Res., 2014, 5(1), 1-17.
[http://dx.doi.org/10.1016/j.jare.2013.01.004] [PMID: 25685467]
[24]
(a) Habibi, A.; Soltanloo, Z.; Beiraghi, A.; Valizadeh, Y. Dyes Pigments, 2015, 113, 481.
[http://dx.doi.org/10.1016/j.dyepig.2014.09.020]
(b) Habibi, A.; Valizadeh, Y.; Alizadeh, A. Helv. Chim. Acta, 2015, 98, 67.
[http://dx.doi.org/10.1002/hlca.201400127]
(c) Habibi, A.; Sheikhhosseini, E.; Taghipoor, N. Chem. Heterocycl. Compd., 2013, 49, 968.
[http://dx.doi.org/10.1007/s10593-013-1333-y]
(d) Habibi, A.; Tarameshloo, Z.; Rostamizadeh, S.; Amani, A.M. Lett. Org. Chem., 2012, 9, 155.
[http://dx.doi.org/10.2174/157017812800167439]
[25]
Shahcheragh, S.M.; Habibi, A.; Khosravi, S. Tetrahedron Lett., 2017, 58, 855.
[http://dx.doi.org/10.1016/j.tetlet.2017.01.057]

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