SYNTHESIS AND CYCLIZATION OF SOME THIOSEMICARBAZIDE DERIVATIVES

Y. Moustafa, Hamed; A. Younis, Mohammed; M. Azab, Mohammed

doi:10.21608/bfszu.2017.31048

SYNTHESIS AND CYCLIZATION OF SOME THIOSEMICARBAZIDE DERIVATIVES

Document Type : Original Article

Authors

¹ Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt

² Department of Chemistry, Faculty of Science, Banha Universty, Banha, Egypt

10.21608/bfszu.2017.31048

Abstract

The thiosemicarbazide 3 was obtained from reaction between hydrazine 2 and heteroallene 1. The condensed triazotriazole derivative 5 was obtained from the reaction of compound 3 with diethyl malonate. The cyclization of thiourea unit of compound 3 by heteroallene 1 furnished triazine 8. Benzoylation of compound 3 using benzoyl chloride 9 formed triazole derivative 11. Reaction of compound 3 and maleic anhydride 12 gave furothiadiazine 13. cyclohexanopyrimidinthione 16 was obtained as a result of cyclocondensation of cyclohexanone 14 with compound 3. Triazole 19 obtained from compound 3 and ammonium isothiocyanate 17 under thermal condition. Reaction of compound 3 with ethyl bromoacetate gave thiazole derivative 22. [2+3] cyclocondensation of acetyl acetone 23 and compound 3 provided pyrazole 25. Triazolotriazole 27 obtained from Formalin 26 and compound 3. Compound 3 suffers intramolecular base mediated cyclization affording triazole 28. Keeping compound 3 and propinaldehyde 29 under reflux provided triazolotriazole 31. Compound 3 oxidized by iodine to oxadiazole 32. Acylation of compound 3 by succinic acid formed triazolthione 34.