Utilization of 2-Ylidene-4-thiazolidinones in Synthesis of Heterocyclic Compounds Part (II): Transformation of (4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile to 3-Aminothiophene Derivatives

M.F. Farhat; M.A. Makhlouf; A.B. Elmezoughi; A.A.M. El-Mehdi; A.M.M. El-Saghier

doi:10.14233/ajchem.2016.19850

Issue

Vol. 28 No. 8 (2016): Vol 28 Issue 8

Issue Published : April 30, 2016

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

Utilization of 2-Ylidene-4-thiazolidinones in Synthesis of Heterocyclic Compounds Part (II): Transformation of (4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile to 3-Aminothiophene Derivatives

https://doi.org/10.14233/ajchem.2016.19850

M.F. Farhat

Chemistry Department, Faculty of Science, Tripoli University, P.O. Box 13494, Tripoli, Libya

M.A. Makhlouf

Chemistry Department, Faculty of Science, Tripoli University, P.O. Box 13494, Tripoli, Libya

A.B. Elmezoughi

Chemistry Department, Faculty of Science, Tripoli University, P.O. Box 13494, Tripoli, Libya

A.A.M. El-Mehdi

Chemistry Department, Faculty of Science and Arts, University of Al-Jabal Al-Gharbi, Gharian, Libya

A.M.M. El-Saghier

Chemistry Department, Faculty of Science, Sohag University, Sohag, Egypt

Corresponding Author(s) : A.M.M. El-Saghier

el_saghier@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 8 (2016): Vol 28 Issue 8
Article Published : April 30, 2016

Abstract

Alkyl 3-aminothiophene carboxylates derivatives (3a-d) were prepared via reaction of (4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile (2) with alcohols. Compound 3a was allowed to react with acetic anhydride, chloroacetyl chloride and nitrous acid to afford N,N,N-triacetylthiophene, 3-chloro-acetamidothiophene and 3-diazothiophene derivatives (6, 7 and 8), respectively. Compound 8 was allowed to react with sodium azide to afford the 3-azidothiophene derivative (9). On the other hand, 3-amino-2-carboxamidothiophene derivatives (10a-c) were prepared via reaction of compound 2 with a variety of amines. Compound 10a was allowed to react with acetic anhydride to afford thieno[3,2d]oxazinone (12).

Keywords

3-Aminothiophene carboxylates Thieno[3,2-d]oxazinone 3-Azidothiophene

Farhat, M., Makhlouf, M., Elmezoughi, A., El-Mehdi, A., & El-Saghier, A. (2016). Utilization of 2-Ylidene-4-thiazolidinones in Synthesis of Heterocyclic Compounds Part (II): Transformation of (4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile to 3-Aminothiophene Derivatives. Asian Journal of Chemistry, 28(8), 1823–1827. https://doi.org/10.14233/ajchem.2016.19850

Download Citation

References

M. Yokoyama, H. Togo and S. Kondo, Sulfur Reports, 10, 23 (1990); doi:10.1080/01961779008048749.
R.K. Dieter, Tetrahedron, 42, 3029 (1986); doi:10.1016/S0040-4020(01)87376-2.
H. Junjappa, H. Ila and C.V. Asokan, Tetrahedron, 46, 5423 (1990); doi:10.1016/S0040-4020(01)87748-6.
M.F. Farhat, A.M.M. El-Saghier, M.A. Makhlouf, K.M. Kreddan and A.B. Elmezoughi, J. Sulfur Chem., 28, 563 (2007); doi:10.1080/17415990701586823.
F.E.M. El-Baih, H.A.S. Al-Blowy and H.M. Al-Hazimi, Molecules, 11, 498 (2006); doi:10.3390/11070498.
R.V. Chambhare, B.G. Khadse, A.S. Bobde and R.H. Bahekar, Eur. J. Med. Chem., 38, 89 (2003); doi:10.1016/S0223-5234(02)01442-3.
N. Hosseinzadeh, M. Hasani, A. Foroumadi, H. Nadri, S. Emami, N. Samadi, M.A. Faramarzi, P. Saniee, F. Siavoshi, N. Abadian, Y. Mahmoudjanlou, A. Sakhteman, A. Moradi and A. Shafiee, Med. Chem. Res., 22, 2293 (2013); doi:10.1007/s00044-012-0224-6.
G.M.K.N. Jayaveera, L.K.R. Nath, B.S. Kumar and P.N. Raddy, J. Chem. Pharm. Res., 4, 2928 (2012).
(a) L.D. Jennings, S.L. Kincaid, Y.D. Wang, G. Krishnamurthy, C.F. Beyer, J.P. McGinnis, M. Miranda, C.M. Discafani and S.K. Rabindran, Bioorg. Med. Chem. Lett., 15, 4731 (2005); doi:10.1016/j.bmcl.2005.07.072; (b) A. Deep, P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R. Mishra and A. Majeed, Curr. Top. Med. Chem., 15, 990 (2015); doi:10.2174/1568026615666150317221849.
M.D. Meyer, R.J. Altenbach, F.Z. Basha, W.A. Carroll, S. Condon, S.W. Elmore, J.F. Kerwin, K.B. Sippy, K. Tietje, M.D. Wendt, A.A. Hancock, M.E. Brune, S.A. Buckner and I. Drizin, J. Med. Chem., 43, 1586 (2000); doi:10.1021/jm990567u.
A. Panico, V. Cardile, A. Santagati and B. Gentile, IL Farmaco, 56, 959 (2001); doi:10.1016/S0014-827X(01)01149-1.
M.F. Farhat, M.A. Makhlouf, A.M. El-Saghier, A.B.A. Mezoughi, S.M. Awhida and A.A.M. El-mehdi, Arabian J. Chem., 4, 307 (2011); doi:10.1016/j.arabjc.2010.06.051.
H. Behbehani and H.M. Ibrahim, Molecules, 17, 6362 (2012); doi:10.3390/molecules17066362.
R.I. Meltzer, A.D. Lewis and J.A. King, J. Am. Chem. Soc., 77, 4062 (1955); doi:10.1021/ja01620a029.
M. Bercot-Vatteroni, Ann. Chim., 7, 303 (1962).
S. Kakimoto, J. Seydel and E. Wempe, Tuberk-Forschunginst. Borstel, Jahresber, 5, 240 (1961).
G. Pappalardo, B. Tornetta, P. Condorelli and A. Bernardini, Farmaco Ed Sci, 22, 808 (1967).
R.V. Davies, Eur. Pat. Appl. EP 269,295 (1988).
F. Russo, A. Santagati, M. Santagati, A. Caruso, M.G. Leone, A. Felice and M. Amico-Roxas, Eur. J. Med. Chem., 24, 91 (1989); doi:10.1016/0223-5234(89)90170-0.
C.J. Shishoo, U.S. Pathak, K.S. Jain, I.T. Devani and M.T. Chhabria, Indian J. Chem., 33B, 436 (1994).
K. Gewald, H. Schaefer and P. Bellmann, German (E) Patent 263,055 (1988).
G. Sommen, A. Comel and G. Kirsch, Fifth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-5), [A0019]; http://www.mdpi.org/ecsoc-5.htm, 1-30 September, 2001.
M.F. Farhat, G.A. Ahmed, A.M.M. El-Saghier, M.A. Makhlouf, W.A. Ehwellat, K.M. Kreddan and A.B. Elmezoughi, In Proceedings of 10th IBN SINA International Conference on Pure and Applied Heterocyclic Chemistry, Luxor, Egypt, Feb. 17-20 (2007).
G.A. Ahmed, Phosphorus Sulfur Silicon Rel. Elem., 183, 74 (2007); doi:10.1080/10426500701557005.

References

M. Yokoyama, H. Togo and S. Kondo, Sulfur Reports, 10, 23 (1990); doi:10.1080/01961779008048749.

R.K. Dieter, Tetrahedron, 42, 3029 (1986); doi:10.1016/S0040-4020(01)87376-2.

H. Junjappa, H. Ila and C.V. Asokan, Tetrahedron, 46, 5423 (1990); doi:10.1016/S0040-4020(01)87748-6.

M.F. Farhat, A.M.M. El-Saghier, M.A. Makhlouf, K.M. Kreddan and A.B. Elmezoughi, J. Sulfur Chem., 28, 563 (2007); doi:10.1080/17415990701586823.

F.E.M. El-Baih, H.A.S. Al-Blowy and H.M. Al-Hazimi, Molecules, 11, 498 (2006); doi:10.3390/11070498.

R.V. Chambhare, B.G. Khadse, A.S. Bobde and R.H. Bahekar, Eur. J. Med. Chem., 38, 89 (2003); doi:10.1016/S0223-5234(02)01442-3.

N. Hosseinzadeh, M. Hasani, A. Foroumadi, H. Nadri, S. Emami, N. Samadi, M.A. Faramarzi, P. Saniee, F. Siavoshi, N. Abadian, Y. Mahmoudjanlou, A. Sakhteman, A. Moradi and A. Shafiee, Med. Chem. Res., 22, 2293 (2013); doi:10.1007/s00044-012-0224-6.

G.M.K.N. Jayaveera, L.K.R. Nath, B.S. Kumar and P.N. Raddy, J. Chem. Pharm. Res., 4, 2928 (2012).

(a) L.D. Jennings, S.L. Kincaid, Y.D. Wang, G. Krishnamurthy, C.F. Beyer, J.P. McGinnis, M. Miranda, C.M. Discafani and S.K. Rabindran, Bioorg. Med. Chem. Lett., 15, 4731 (2005); doi:10.1016/j.bmcl.2005.07.072; (b) A. Deep, P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R. Mishra and A. Majeed, Curr. Top. Med. Chem., 15, 990 (2015); doi:10.2174/1568026615666150317221849.

M.D. Meyer, R.J. Altenbach, F.Z. Basha, W.A. Carroll, S. Condon, S.W. Elmore, J.F. Kerwin, K.B. Sippy, K. Tietje, M.D. Wendt, A.A. Hancock, M.E. Brune, S.A. Buckner and I. Drizin, J. Med. Chem., 43, 1586 (2000); doi:10.1021/jm990567u.

A. Panico, V. Cardile, A. Santagati and B. Gentile, IL Farmaco, 56, 959 (2001); doi:10.1016/S0014-827X(01)01149-1.

M.F. Farhat, M.A. Makhlouf, A.M. El-Saghier, A.B.A. Mezoughi, S.M. Awhida and A.A.M. El-mehdi, Arabian J. Chem., 4, 307 (2011); doi:10.1016/j.arabjc.2010.06.051.

H. Behbehani and H.M. Ibrahim, Molecules, 17, 6362 (2012); doi:10.3390/molecules17066362.

R.I. Meltzer, A.D. Lewis and J.A. King, J. Am. Chem. Soc., 77, 4062 (1955); doi:10.1021/ja01620a029.

M. Bercot-Vatteroni, Ann. Chim., 7, 303 (1962).

S. Kakimoto, J. Seydel and E. Wempe, Tuberk-Forschunginst. Borstel, Jahresber, 5, 240 (1961).

G. Pappalardo, B. Tornetta, P. Condorelli and A. Bernardini, Farmaco Ed Sci, 22, 808 (1967).

R.V. Davies, Eur. Pat. Appl. EP 269,295 (1988).

F. Russo, A. Santagati, M. Santagati, A. Caruso, M.G. Leone, A. Felice and M. Amico-Roxas, Eur. J. Med. Chem., 24, 91 (1989); doi:10.1016/0223-5234(89)90170-0.

C.J. Shishoo, U.S. Pathak, K.S. Jain, I.T. Devani and M.T. Chhabria, Indian J. Chem., 33B, 436 (1994).

K. Gewald, H. Schaefer and P. Bellmann, German (E) Patent 263,055 (1988).

G. Sommen, A. Comel and G. Kirsch, Fifth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-5), [A0019]; http://www.mdpi.org/ecsoc-5.htm, 1-30 September, 2001.

M.F. Farhat, G.A. Ahmed, A.M.M. El-Saghier, M.A. Makhlouf, W.A. Ehwellat, K.M. Kreddan and A.B. Elmezoughi, In Proceedings of 10th IBN SINA International Conference on Pure and Applied Heterocyclic Chemistry, Luxor, Egypt, Feb. 17-20 (2007).

G.A. Ahmed, Phosphorus Sulfur Silicon Rel. Elem., 183, 74 (2007); doi:10.1080/10426500701557005.

Issue

Vol. 28 No. 8 (2016): Vol 28 Issue 8

Utilization of 2-Ylidene-4-thiazolidinones in Synthesis of Heterocyclic Compounds Part (II): Transformation of (4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile to 3-Aminothiophene Derivatives

Corresponding Author(s) : A.M.M. El-Saghier

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents