Synthesis and Characterization of Some 5-Substituted 2-Thiol/Thione-1,3,4-Oxadiazoles

Zeid Hassan Abood

doi:10.14233/ajchem.2016.19899

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Issue Published : September 1, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Characterization of Some 5-Substituted 2-Thiol/Thione-1,3,4-Oxadiazoles

https://doi.org/10.14233/ajchem.2016.19899

Zeid Hassan Abood

Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq

Corresponding Author(s) : Zeid Hassan Abood

zeid.ab2013@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 12 (2016): Vol 28 Issue 12
Article Published : September 2, 2016

Abstract

5-(4-Aminophenyl)-2-thiol-1,3,4-oxadiazole (1) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide. Compound 1 was converted to the corresponding diazonium salt which was introduced in coupling reaction with sodium phenoxide as coupling reagent to give azooxadiazole derivative containing aldehyde group 2. The resulting aldehyde 2 was then introduced in acid-catalyzed condensation reactions with both 2-aminobenzothiazole and 2-amino-5-mercapto-1,3,4-thiadiazole to obtain the oxadiazolic-imines 3a and 3b, respectively. Treatment of the resulting imines 3a and 3b with each succinic acid, maleic acid, phthalic acid and 3-nitrophthalic anhydrides, respectively, under (2+5) cycloaddition conditions afforded eight new oxadiazoles substituted with 1,3-oxazepane and 1,3-oxazepine moieties 4a-d and 5a-d, respectively. The resulting imines 3a and 3b were also treated with sodium azide under (2+3) cycloaddition conditions to obtain two new oxadiazoles containing tetrazole moiety 4e and 5e, respectively. The newly synthesized oxadiazoles might have some biological, pharmaceutical and medicinal applications.

Keywords

1,3,4-Oxadiazoles Imines 1,3-Oxazepanes 1,3-Oxazepines Tetrazoles Azo

Abood, Z. H. (2016). Synthesis and Characterization of Some 5-Substituted 2-Thiol/Thione-1,3,4-Oxadiazoles. Asian Journal of Chemistry, 28(12), 2582–2588. https://doi.org/10.14233/ajchem.2016.19899

Download Citation

References

C.V. Maftei, E. Fodor, P.G. Jones, M.H. Franz, G. Kelter, H. Fiebig and I. Neda, Beilstein J. Org. Chem., 9, 2202 (2013); doi:10.3762/bjoc.9.259.
C.K. Nagaraj, M.S. Niranjan and S. Kiran, Int. J. Pharm. Pharm. Sci., 3, 9 (2011).
D.A. Cooper, R.T. Steigbigel, J.M. Gatell, J.K. Rockstroh, C. Katlama, P. Yeni, A. Lazzarin, B. Clotet, P.N. Kumar, J.E. Eron, M. Schechter, M. Markowitz, M.R. Loutfy, J.L. Lennox, J. Zhao, J. Chen, D.M. Ryan, R.R. Rhodes, J.A. Killar, L.R. Gilde, K.M. Strohmaier, A.R. Meibohm, M.D. Miller, D.J. Hazuda, M.L. Nessly, M.J. DiNubile, R.D. Isaacs, H. Teppler and B.-Y. Nguyen, N. Engl. J. Med., 359, 355 (2008); doi:10.1056/NEJMoa0708978.
N.B. Patel and J.C. Patel, Sci. Pharm., 78, 171 (2010); doi:10.3797/scipharm.0912-16.
V.K. Sahu, A.K. Singh and D. Yadav, Int. J. Chem. Tech. Res., 3, 1362 (2011).
K. Selvaraj, G. Sadhasivam and K. Kulanthai, Asian J. Pharm. Clin. Res., 7, 11 (2014).
Y. Selim and N. Ouf, Org. Med. Chem. Lett., 2, 1 (2012); doi:10.1186/2191-2858-2-1.
C. Sowjanya, V.R. Bharathi, G.K. Devi and G. Rajitha, J. Chem. Pharm. Res., 3, 212 (2011).
A. Martin, Int. J. Pharmaceut. Biol. Sci. Arch., 1, 87 (2013).
M.C. Hosur, M.B. Talawar and U.V. Lada, Indian J. Heterocycl. Chem., 3, 237 (1994).
W.S. El-Hamouly, K.M. Amin, S.A. El-Assaly and E.A.A. El-Meguid, Der Pharma Chemica, 3, 282 (2011).
K. Nagarajan, J. David, Y.S. Kulkarni, S.B. Hendi, S.J. Shenoy and P. Upadhyaya, Eur. J. Med. Chem., 21, 21 (1986).
Y. Liao, B.J. Venhuis, N. Rodenhuis, W. Timmerman, H. Wikstrom, E. Meier, G.D. Bartoszyk, H. Böttcher, C.A. Seyfried and S. Sundell, J. Med. Chem., 42, 2235 (1999); doi:10.1021/jm991005d.
M. Sahu, A.G. Nerkar, H.U. Chikhale and S.D. Sawant, J. Young Pharmacists, 7, 21 (2015).
B. Hüe, B. Palomba, M. Giacardy-Paty, T. Bottaï, R. Alric and P. Petit, Ther. Drug Monit., 20, 335 (1998); doi:10.1097/00007691-199806000-00016.
S.S. Schweiker, W.A. Loughlin, A.S. Lohning, M.J. Petersson and I.D. Jenkins, Eur. J. Med. Chem., 84, 584 (2014); doi:10.1016/j.ejmech.2014.07.063.
K. Bera, S. Jalal, S. Sarkar and U. Jana, Org. Biomol. Chem., 12, 57 (2014); doi:10.1039/C3OB41624K.
M.C. Sleevi, A.D. Cale Jr., T.W. Gero, L.W. Jaques, W.J. Welstead, A.F. Johnson, B.F. Kilpatrick, I. Demian, J.C. Nolan and H. Jenkins, J. Med. Chem., 34, 1314 (1991); doi:10.1021/jm00108a012.
Y. Liu, C. Chu, A. Huang, C. Zhan, C. Ma and C. Ma, ACS Comb. Sci., 13, 547 (2011); doi:10.1021/co2001058.
J.M. Kane, B.M. Baron, M.W. Dudley, S.M. Sorensen, M.A. Staeger and F.P. Miller, J. Med. Chem., 33, 2772 (1990); doi:10.1021/jm00172a015.
K. Samanta, B. Chakravarti, J.K. Mishra, S.K.D. Dwivedi, L.V. Nayak, P. Choudhry, H.K. Bid, R. Konwar, N. Chattopadhyay and G. Panda, Bioorg. Med. Chem. Lett., 20, 283 (2010); doi:10.1016/j.bmcl.2009.10.115.
S. Muralikrishna, P.R. Reddy, L.K. Ravindranath, S. Harikrishna and P.J. Rao, Int. J. Pharma Res. Rev., 3, 58 (2014).
A.P. Ingale, J. Chem. Pharm. Res., 6, 460 (2014).
R.E. Ford, P. Knowles, E. Lunt, S.M. Marshall, A.J. Penrose, C.A. Ramsden, A.J.H. Summers, J.L. Walker and D.E. Wright, J. Med. Chem., 29, 538 (1986); doi:10.1021/jm00154a019.
M. Arshad, A.R. Bhat, S. Pokharel, J.E. Kim, E.J. Lee, F. Athar and I. Choi, Eur. J. Med. Chem., 71, 229 (2014); doi:10.1016/j.ejmech.2013.11.008.
R.W. Young and K.H. Wood, J. Am. Chem. Soc., 77, 400 (1955); doi:10.1021/ja01607a051.
Q.A. Acton, Azo Compounds: Advances in Research and Application, Scholarly Paper Edition, Atlanta, p. 42 (2011).

References

C.V. Maftei, E. Fodor, P.G. Jones, M.H. Franz, G. Kelter, H. Fiebig and I. Neda, Beilstein J. Org. Chem., 9, 2202 (2013); doi:10.3762/bjoc.9.259.

C.K. Nagaraj, M.S. Niranjan and S. Kiran, Int. J. Pharm. Pharm. Sci., 3, 9 (2011).

D.A. Cooper, R.T. Steigbigel, J.M. Gatell, J.K. Rockstroh, C. Katlama, P. Yeni, A. Lazzarin, B. Clotet, P.N. Kumar, J.E. Eron, M. Schechter, M. Markowitz, M.R. Loutfy, J.L. Lennox, J. Zhao, J. Chen, D.M. Ryan, R.R. Rhodes, J.A. Killar, L.R. Gilde, K.M. Strohmaier, A.R. Meibohm, M.D. Miller, D.J. Hazuda, M.L. Nessly, M.J. DiNubile, R.D. Isaacs, H. Teppler and B.-Y. Nguyen, N. Engl. J. Med., 359, 355 (2008); doi:10.1056/NEJMoa0708978.

N.B. Patel and J.C. Patel, Sci. Pharm., 78, 171 (2010); doi:10.3797/scipharm.0912-16.

V.K. Sahu, A.K. Singh and D. Yadav, Int. J. Chem. Tech. Res., 3, 1362 (2011).

K. Selvaraj, G. Sadhasivam and K. Kulanthai, Asian J. Pharm. Clin. Res., 7, 11 (2014).

Y. Selim and N. Ouf, Org. Med. Chem. Lett., 2, 1 (2012); doi:10.1186/2191-2858-2-1.

C. Sowjanya, V.R. Bharathi, G.K. Devi and G. Rajitha, J. Chem. Pharm. Res., 3, 212 (2011).

A. Martin, Int. J. Pharmaceut. Biol. Sci. Arch., 1, 87 (2013).

M.C. Hosur, M.B. Talawar and U.V. Lada, Indian J. Heterocycl. Chem., 3, 237 (1994).

W.S. El-Hamouly, K.M. Amin, S.A. El-Assaly and E.A.A. El-Meguid, Der Pharma Chemica, 3, 282 (2011).

K. Nagarajan, J. David, Y.S. Kulkarni, S.B. Hendi, S.J. Shenoy and P. Upadhyaya, Eur. J. Med. Chem., 21, 21 (1986).

Y. Liao, B.J. Venhuis, N. Rodenhuis, W. Timmerman, H. Wikstrom, E. Meier, G.D. Bartoszyk, H. Böttcher, C.A. Seyfried and S. Sundell, J. Med. Chem., 42, 2235 (1999); doi:10.1021/jm991005d.

M. Sahu, A.G. Nerkar, H.U. Chikhale and S.D. Sawant, J. Young Pharmacists, 7, 21 (2015).

B. Hüe, B. Palomba, M. Giacardy-Paty, T. Bottaï, R. Alric and P. Petit, Ther. Drug Monit., 20, 335 (1998); doi:10.1097/00007691-199806000-00016.

S.S. Schweiker, W.A. Loughlin, A.S. Lohning, M.J. Petersson and I.D. Jenkins, Eur. J. Med. Chem., 84, 584 (2014); doi:10.1016/j.ejmech.2014.07.063.

K. Bera, S. Jalal, S. Sarkar and U. Jana, Org. Biomol. Chem., 12, 57 (2014); doi:10.1039/C3OB41624K.

M.C. Sleevi, A.D. Cale Jr., T.W. Gero, L.W. Jaques, W.J. Welstead, A.F. Johnson, B.F. Kilpatrick, I. Demian, J.C. Nolan and H. Jenkins, J. Med. Chem., 34, 1314 (1991); doi:10.1021/jm00108a012.

Y. Liu, C. Chu, A. Huang, C. Zhan, C. Ma and C. Ma, ACS Comb. Sci., 13, 547 (2011); doi:10.1021/co2001058.

J.M. Kane, B.M. Baron, M.W. Dudley, S.M. Sorensen, M.A. Staeger and F.P. Miller, J. Med. Chem., 33, 2772 (1990); doi:10.1021/jm00172a015.

K. Samanta, B. Chakravarti, J.K. Mishra, S.K.D. Dwivedi, L.V. Nayak, P. Choudhry, H.K. Bid, R. Konwar, N. Chattopadhyay and G. Panda, Bioorg. Med. Chem. Lett., 20, 283 (2010); doi:10.1016/j.bmcl.2009.10.115.

S. Muralikrishna, P.R. Reddy, L.K. Ravindranath, S. Harikrishna and P.J. Rao, Int. J. Pharma Res. Rev., 3, 58 (2014).

A.P. Ingale, J. Chem. Pharm. Res., 6, 460 (2014).

R.E. Ford, P. Knowles, E. Lunt, S.M. Marshall, A.J. Penrose, C.A. Ramsden, A.J.H. Summers, J.L. Walker and D.E. Wright, J. Med. Chem., 29, 538 (1986); doi:10.1021/jm00154a019.

M. Arshad, A.R. Bhat, S. Pokharel, J.E. Kim, E.J. Lee, F. Athar and I. Choi, Eur. J. Med. Chem., 71, 229 (2014); doi:10.1016/j.ejmech.2013.11.008.

R.W. Young and K.H. Wood, J. Am. Chem. Soc., 77, 400 (1955); doi:10.1021/ja01607a051.

Q.A. Acton, Azo Compounds: Advances in Research and Application, Scholarly Paper Edition, Atlanta, p. 42 (2011).

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Synthesis and Characterization of Some 5-Substituted 2-Thiol/Thione-1,3,4-Oxadiazoles

Corresponding Author(s) : Zeid Hassan Abood

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents