A new facile route to synthesize thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives

Soleimany, Mehdi; Lari, Jalil; Vahedi, Hooshang; Imanpour, Morteza

Document Type : Original Research Article

Authors

¹ Payame Noor University (PNU)

² Payame Noor University of Mashhad

Abstract

A new facile route for synthesis of 3- (aryl) -8, 9- di (alkyl) thieno [3,2-e] [1,2,4] triazolo pyrimidines derivative from the same starting material, 2- amino - 4,5 -di (alkyl) thiophene-3- carboxamide, has been developed through heterocyclization of the corresponding arylidene-hydrazino -5,6 -di (alkyl) thieno [2,3-d] pyrimidine under refluxing condition with acetic anhydride followed by air oxidation. The products were obtained in high yield with an easy work-up in simple reaction along with the puriﬁcation of products by non-chromatographic method. This general synthetic procedure can be extended to the preparation of a wide variety of isomeric triazoles using 2-amino thiophene-3-carboxamide bifunctional derivatives.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] D.J. Brown, Pyrimidines and Their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry (Eds. A.R. Katritzky and C.W. Rees), Pergamon Press, Oxford, 1984, 3, 443-495.

[2] B. Roth, C. Cheng, Progress in Medicinal chemistry (Eds. G.P. Ellis and G.B. West), Elsevier Biomedical Press, New York, 1982, 19, 267-278.

[3] C.R. Petrie, H.B. Cottam, P.A. Mckernan, R.K. Robins, G.R. Revankar, J. Med. Chem., 1985, 28, 1010–1016.

[4] M.S.A.E.-A. El-Gaby, S.G. Abdel-Hamide, M.M. Ghorab, S.M. El-Sayed, Acta Pharm., 1999, 49, 149–158.

[5] M.N. Nasr, M.M. Gineinah, Arch. Pharm., 2002, 335, 289–295.

[6] P.G. Baraldi, M.G. Pavani, M. Nunez, P. Brigidi, B. Vitali, R. Gambari, R. Romagnoli, Bioorg. Med. Chem., 2002, 10, 449–456.

[7] S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir, J.W. Lown, Australian J. Chem., 2001, 54, 69–74.

[8] A.Z.M.S. Chowdhury, M.M. Matin, M.N. Anwar, Chittagong Univ. Stud. Part II: Sci. 1997, 21, 79–83; ref. Chem. Abstr. 1999, 130, 237530p.

[9] G. Mangalagiu, M. Ungureanu, G. Grosu, I. Mangalagiu, M. Petrovanu, Ann. Pharm. Fr., 2001, 59, 139–140.

[10] C.J. Shishoo, V.S. Shirsath, I.S. Rathod, M.J. Patil, S.S. Bhargava, Arzneim. Forsch., 2001, 51, 221–231.

[11] O. Bruno, C. Brullo, S. Schenone, A. Ranise, F. Bondavalli, E. Barocelli, M. Tognolini, F. Magnanini, V. Bollabeni, Farmaco., 2002, 57, 753-758.

[12] Kh.M. Al-Taisan, H.M.A. Al-Hazimi, Sh.S. Al-Shihry, Molecules., 2010, 15, 3932-3957.

[13] M.R. Prasad, A.R. Rao, P.Sh. Rao, K.S. Rajan, Sh. Meena, K. Madhavi, Eur. J. Med. Chem., 2008, 43, 614-620.

[14] M.A. Gouda, M.A. Berghot, Gh.E. Abd El-Ghani, Kh.M. Elattar, A.E.G.M. Khalil, Turk. J. Chem., 2011, 35, 815-837.

[15] Shakhashiri, Z. Bassam, "Acetic Acid & Acetic Anhydride", Science is Fun… (Department of Chemistry, University of Wisconsin), retrieved 2006-03-25.

[16] Acetic anhydride, SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, p. 5

[17] Davoodnia, A.; Bakavoli, M.; Soleimany, M.; Tavakoli-Hoseini, N. Monatsh. Chem., 2009, 140, 355-358.

[18] K. Gewald, E. Schinke, H. Bottcher, Chem. Ber., 1966, 99, 94–100.

[19] A. Davoodnia, M. Bakavoli, G. Barakouhi, N. Tavakoli-Hoseini, Chinese. Chem. Lett., 2007, 18, 1483-1486.

[20] M.I. Hossain, M.M.H. Bhuiyan, J. Sci. Res., 2009, 1, 317-325.

[21] V.J. Ram, Arch. Pharm., 1979, 312, 19-25.

[22] V.J. Ram, J. Heterocycl. Chem., 1981, 18, 1277-1280.

Iranian chemical communication

A new facile route to synthesize thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 114-120

A new facile route to synthesize thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7April 2015Pages 114-120

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 114-120