Synthesis and Characterization of some new 2,5-disubstituted- 1,3,4-oxadiazole derivatives Containing Antipyrine moiety.

Mohammad Amin Mohammad Rashid and Sewara Jalal MohammedMohammed
Faculty of Science and Science Education, School of Science, Department of Chemistry, University of Sulaimani, Kurdistan region, Iraq


Abstract

Some new 2,5-disubstituted-1,3,4-oxadiazolels of type (E)-4-((1-(5-(substitutedphenyl)
1,3,4-oxadiazol-2-yl)pro-1-en-2-yl)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-
one were synthesized in (60-81%) yield under solvent free conditions using grinding
technique through the reaction of hydrazide intermediate with benzaldehyde or different
substituted benzaldehydes in the presence of catalytic amounts of iodine molecular as a
single step. The structures of all the synthesized compounds were confirmed on the basis
of their physical properties, IR, 1H-NMR and Mass spectral data.

Key words:
4-Aminoantipyrine
Ethyl acetoacetate
Enaminone
Hydrazide
Oxadiazole derivatives


References

[1] Katritzky A. R., Ramsden C. A., Scriven E. F. V., Taylor R. J. K. Eds. In Comprehensive Heterocyclic Chemistry III; Elsevier: Oxford. , 3, (2008)

[2] Gil C., Bräse S. J. Comb. Chem. , 9, PP. 175 ,(2009).

[3] Carey J. S., Laffan D., Thomson C., Williams M. T. Org. Biomol. Chem., 4, PP. 2337, (2006).

[4] Dömling A. Chem. Rev. , 106, PP.17 , (2006).

[5] Rück-Braun K., Freysoldt T. H. E., Wierschem F. Chem. Soc. Rev. , 34, PP.507, (2005).

[6] O’Mahony G. E., Kelly P., Lawrence S. E., Maguire A. R. Arkivoc , (i), PP.1,(2011).

[7] Patli S.G. ; Badiger M.;Kudari S.M. and Purohit M.G., Indian J.Heterocyclic Chem.,17,PP.37, (2007). 

[8] Sridhara AM ; Reddy KRV; Keshavayya J; Goud PSK; Somashekar BC and Bose P., Eur J Med Chem., 45, PP.4983, (2010). 

[9] Dhansay D ;Alok P; Sivakumar T; Rajavel D and Dhar D., International Journal of Chem Tech Research. ,2,PP.1397, (2010). 

[10] Manish S; Deepak S; Aashish Singh K and Gokulan P., Journal of Current Pharmaceutical Research. ,4,PP.20 ,(2010). 

[11] Elmagd W.S.I.A. ;Hashem A.I.; Youssef A.S.A and Kandeel K.A., Eur. J. Med Chem. ,42(7),PP. 934, (2007).

[12] Ali A; EI-Emam ; Omer A; AL-Deeb A. ;Mohamed A and Jochen L. Bioorganic and Medicinal Chemistry. ,12, PP.5107, (2004). 

[13] Sanmati K ; Arvind K and Pragya N., International Journal of Pharmaceutical Sciences and Drug Research. , 3,PP.230 ,(2011). 

[14] Harish R; Murli D ;Kharya B and Pradeep M., Indian Journal of Chemistry. , 45 , PP.2506, (2006). 

[15] Sudhir B; Bharat P; Narendra P and Sharma V., Archives of Applied Science Research., 3,PP.558,(2011) 

[16] Ariffin A and Abdulla M.A., Molecules, 19,PP.3436, (2014). 

[17] Kagthara PR; Shah NS; Doshi RK and Parekh HH. , Indian J Chem. , 38B,PP.572, (1999). 

[18] Maillard J; Vincent M; Morin R and Bernard M., French Pat. M379.Chem Abstr. 1962,57,15251g 

[19] Ravindra K.C.; Vogdevi M and Vaidya V.P., Indian J Chem,B,42, PP.2506, (2006). 

[20] Ravitas D; Jha A.K; Alok Singh T and Dhansay D., International Journal of Research in Pharmaceutical and Biomedical Sciences , 2, PP.215, (2011).

[21] Nagaraj Chaluvaraju K; Niranjan M and Kiran S .,International Journal of Pharmacy and Pharmaceutical Science , 3, PP.8, (2011). 

[22] Sahin E; Kelicen P.C; Demiradamar R and Altinok G.,ArzneimForsch Drug Res., 51,PP. 478, (2001). 

[23] Mohan TP; VishalakshiB,Bhat KS and Kendappa GN., Indian J Chem. , 43B,PP. 1798 ,(2004). 

[24] Kennedy DA , and Summers LA., J Heterocyclic Chem. , 18,PP.409 ,(1981). 

[25] Chauhn D; Chauhan JS; Singh J; Bajpai SK and Joshi MN., Indian J.Chem., 42B, PP.215, (2003). 

[26] Bharathi D; Hemalatha S; Devadass G; Kumar PR; Shanmugasundaram P and Aanandhi MV., International Journal of Chem Tech Research .,2(4),PP.1867, (2010). 

[27] Yale HI and Losee K., J Med Chem. , 9,PP.478, (1966). 

[28] Silvio Cunha; Shana M. Oliveira; Manoel T. Rodrigues Jr.; Rodrigo M. Bastos; JailtonFerrar; Cecı´lia M.A. de Oliveira; Lucı´lia Kato; Hamilton B. Napolitano; Ivo Vencato and CarlitoLariucci., Journal of Molecular Structure., 752 , PP.32–39, (2005). 

[29] Rajasekar K.; Ramachandramoorthy T. and Balasubramaniyan S. ,Chem.Sci. Trans., 2(3), pp. 877-882, (2013)