Microwave Assisted, One Pot Synthesis of Alkyl-3-amino-2-arylimino-1,3-thiazolan-4-ones-5-ylidene Acetate

Kh. Pourshamsian; N. Montazeri; S. Ahamadi; T. Noghani

doi:10.14233/ajchem.2013.13012B

Issue

Vol. 25 No. 1 (2013): Vol 25 Issue 1

Issue Published : August 6, 2012

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

Microwave Assisted, One Pot Synthesis of Alkyl-3-amino-2-arylimino-1,3-thiazolan-4-ones-5-ylidene Acetate

https://doi.org/10.14233/ajchem.2013.13012B

Kh. Pourshamsian

Departement of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

N. Montazeri

Departement of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

S. Ahamadi

Departement of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

T. Noghani

Departement of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Corresponding Author(s) : Kh. Pourshamsian

kh_pourshamsian@toniau.ac.ir

Asian Journal of Chemistry, Vol. 25 No. 1 (2013): Vol 25 Issue 1
Article Published : August 16, 2012

Abstract

Reaction of 4-phenylthiosemicarbazide and thiosemicarbazide with dialkyl acetylene dicarboxylate in CH₂Cl₂ at microwave irradiation lead to alkyl-3-amino-2-phenyliminothiazolidine-4-one-5-ylidene acetate and alkyl-3-amino 2-iminothiazolidine-4-one-5-ylidene acetate in moderate yields and short times. Di-t-butylacetylenedicarboxylate have a different treatment and the cyclization products is not observed. The structures of the synthesized compounds were elucidated by elemental analysis and spectral data.

Keywords

Microwave irradiation Thiazolidine-4-one 4-Phenylthiosemicarbazide Thiosemicarbazide

Pourshamsian, K., Montazeri, N., Ahamadi, S., & Noghani, T. (2012). Microwave Assisted, One Pot Synthesis of Alkyl-3-amino-2-arylimino-1,3-thiazolan-4-ones-5-ylidene Acetate. Asian Journal of Chemistry, 25(1), 306–308. https://doi.org/10.14233/ajchem.2013.13012B

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References

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S.J. Shah, S.R. Shah and N.C. Desai, J. Indian Chem. Soc., 61, 648 (1984).
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M.H. Shih and F.Y. Ke, Bioorg. Med. Chem., 12, 4633 (2004).
A. Rao and A. Carbone, IL Farmaco., 57, 747 (2002).
R. Lakhan and R.L. Singh, J. Agric. Food Chem., 39, 580 (1991).
V. Murugesan, V.S. Tiwari, R. Saxena, R. Tripathi, R. Paranjape, S. Kulkarni, N. Makwana, R. Suryawanshi and S.B. Katti, Bioorg. Med. Chem., 19, 6919 (2011).
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References

G.R. Newkome and A. Nayak, Adv. Heterocycl. Chem., 25, 83 (1979).

S.J. Shah, S.R. Shah and N.C. Desai, J. Indian Chem. Soc., 61, 648 (1984).

M.P. Dave, J.M. Patel and N.L. Langalia, J. Indian Chem. Soc., 61, 891 (1984).

R.J. Boyce and G.C. Mulqeen, Tetrahedron Lett., 35, 5705 (1994).

N. Karali, E. Ilhan,A. Gursoy and M. Kiraz, IL Farmaco, 53, 346 (1998).

H.T. Fahmy, Boll. Chim. Farm., 140, 422 (2001).

C.J. Andres, J.J. Bronson, S.V. D'Andrea, M.S. Deshpande, P.J. Falk, K.A. Grant-Young and W.E. Harte, Bioorg. Med. Chem. Lett., 10, 715 (2000).

S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002).

N. Ergenc and G. Capan, IL Farmaco, 49, 133 (1994).

G. Capan, N. Ergenc, A.C. Ekinci and A. Vidin,IL Farmaco, 51, 729 (1996).

G.C. Look, J.R. Schullek, C.P. Homes, J.P. Chinn, E.M. Ordon and M.A. Gallop, Bioorg. Med. Chem. Lett., 6, 707 (1996).

J.J. Bhatt, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia and N.C. Desai, Indian J. Chem., 33, 189 (1994).

L. Bukowski, M. Janowiec, Z. Zwolska-Kwiek, Z. Andrezejczyk, Pharmazie, 53, 373 (1998).

F.L. Gouveia, R.M.B. de Oliveira, T.B. de Oliveira, I.M. da Silva, S.C. do Nascimento, K.X.F.R. de Sena, J.F.C. de Albuquerque, Eur. J. Med. Chem., 44, 2038 (2009).

N. Ulusoy, Arzneim-Forsch-Drug Res., 52, 565 (2002).

K. Babaoglu, M.A. Page, V.C. Jones, M.R. McNeil, C. Dong, J.H. Naismith and R.E. Lee, Bioorg. Med. Chem. Lett., 13, 3227 (2003).

M.V. Diurno, O. Mazzoni, P.E. Calignano, F. Giordano and A. Bolognese, J. Med. Chem., 35, 2910 (1992).

M.L. Barreca, A. Chimirri, L. De Luca, A.M. Monforte, P. Monforte, A. Rao and M. Zappala, Bioorg. Med. Chem. Lett., 11, 1793 (2001).

M.L. Barreca, J. Balzarini, A. Chimirri, E. De Clercq, L. De Luca, H.D. Holtje, M. Holtje, A.M. Monforte, P. Monforte, C. Pannecouque, A. Rao and M. Zappala, J. Med. Chem., 45, 5410 (2002).

J. Balzarini, B. Orzeszko, J.K. Maurin and A. Orzeszko, Eur. J. Med. Chem., 42, 993 (2007).

J. Balzarini, B. Orzeszko-Krzesin'ska, J.K. Maurin, A. Orzesz, Eur. J. Med. Chem., 44, 303 (2009).

E. De Clercq, Trends Pharmacol. Sci., 11, 198 (1990).

E. De Clercq, J. Med. Chem., 48, 1297 (2005).

P. Wipf and P.C. Fritch, Tetrahedron Lett., 35, 5397 (1994).

J.Y. Lai, J. Yu and B. Mekonnen, Tetrahedron Lett., 37, 7167 (1996).

M.H. Shih and F.Y. Ke, Bioorg. Med. Chem., 12, 4633 (2004).

A. Rao and A. Carbone, IL Farmaco., 57, 747 (2002).

R. Lakhan and R.L. Singh, J. Agric. Food Chem., 39, 580 (1991).

V. Murugesan, V.S. Tiwari, R. Saxena, R. Tripathi, R. Paranjape, S. Kulkarni, N. Makwana, R. Suryawanshi and S.B. Katti, Bioorg. Med. Chem., 19, 6919 (2011).

S.G. Modha and V.P. Mehta, Mol. Divers, 14, 767 (2010).

A. Rao, J. Balzarini and A. Chimirri, IL Farmaco, 59, 33 (2004).

I. Yavari, Z. Hossaini, M. Sabbaghan, K. Porshamsian, M. Bagheri and S. Ali-Asgari, Mol. Divers, 11, 81 (2007).

I. Yavari, K. Porshamsian, M. Bagheri and S. Ali-Asgari, J. Sulfur Chem., 28, 1 (2007).

Kh. Pourshamsian, N. Montazeri, Rad-Moghadam and K.S. Aliasgari, J. Heterocycl. Chem., 47, 1439 (2010).

Issue

Vol. 25 No. 1 (2013): Vol 25 Issue 1

Microwave Assisted, One Pot Synthesis of Alkyl-3-amino-2-arylimino-1,3-thiazolan-4-ones-5-ylidene Acetate

Corresponding Author(s) : Kh. Pourshamsian

Abstract

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