3,5-difenil-1h-1,2,4-triazol halkası içeren yeni heterosiklik bileşiklerin sentezi

Abstract

Bu çalışmada, 3,5-difenil-1H-1,2,4-triazol (46) bileşiğinden başlanarak 1-(4-substituebenzil)-3,5-difenil-1H-1,2,4-triazol'ler (60-64) sentezlendi. Ayrıca, 46 bileşiğinin etilbromoasetatla muamelesi ile elde edilen etil(3,5-difenil-1H-1,2,4-triazol-1-il)asetat (76) bileşiğinin 1-butanol'lü ortamda hidrazin hidrat ile reaksiyonu sonucu 2-(3,5-difenil-1H-1,2,4-triazol-1-il)asetohidrazit (77) bileşiği sentezlendi. 77 bileşiğinin izotiyosiyanatlar ile muamelesinden 2-[(3,5-difenil-1H-1,2,4-triazol-1-il)asetil]4-metil/fenil tiyosemikarbazit (106 ve 107) bileşikleri sentezlendi. Tiyosemikarbazitlerin (106 ve 107) 2N NaOH'li ortamda siklizasyonu sonucunda 5-[(3,5-difenil-1H-1,2,4-triazol-1-il)metil]-4-metil/fenil-2,4-dihidro-3H-1,2,4-triazol-3-tiyol (108 ve 109) bileşikleri oluştu. 108 ve 109 bileşiklerin benzil bromür türevleri (55-59) ile reaksiyonundan 5-[(3,5-difenil-1H-1,2,4-triazol-1-il)metil]-3-(4-substituebenzil)tiyo-4-metil/fenil-2,4-dihidro-3H-1,2,4-triazol (126-135) bileşikleri elde edildi. 21 adet 3,5-difenil-1H-1,2,4-triazol halkası içeren yeni heterosiklik bileşik sentezlendi ve yapıları IR, 1H NMR, 13C NMR ve Kütle spektroskopileri kullanılarak aydınlatılmıştır.

In this study, 1-(4-substitutedbenzyl)-3,5-diphenyl-1H-1,2,4-triazoles (60-64) were synthesized starting from 3,5-diphenyl-1H-1,2,4-triazole (46). Treatment of compound 46 with ethyl bromoacetate obtained ethyl(3,5-diphenyl-1H-1,2,4-triazole-1-yl)acetate (76), which was converted to 2-(3,5-diphenyl-1H-1,2,4-triazole-1-yl)acetohydrazide (77) by treatment with hydrazine hydrate in 1-butanol. 2-[(3,5-diphenyl-1H-1,2,4-triazole-1-yl)acetyl]4-methyl/phenyl thiosemicarbazides (106 and 107) was prepared by the reaction of compound 77 with isothiocyanate derivatives. Cyclization of 106 and 107 with 2N NaOH resulted in the formation of 5-[(3,5-diphenyl-1H-1,2,4-triazole-1-yl)methyl]-4-methyl/phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiole (108 ve 109). Treatment of 108 and 109 with benzyl bromide derivatives (55-59) gave 5-[(3,5-diphenyl-1H-1,2,4-triazole-1-yl)methyl]-3-(4-substitutedbenzyl)thio-4-methyl/phenyl-2,4-dyhidro-3H-1,2,4-triazoles (126-135). Twenty one new heterocyclic compounds containing 3,5-diphenyl-1H-1,2,4-triazole ring were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectra.