1,2,4-triazolin-3-tiyonlardan türeyen bazı tiyoüre bileşikleri üzerinde çalışmalar

Abstract

69 SUMMARY Studies on some thiourea derivatives obtained from l,2,4-triazoline-3-thiones In this study, l-[4-(benzoylamino) benzoyl]-4-methylthiosemicar- bazide (3a) and l-[4-(benzoylamino) benzoyl]-4-phenyl-thiosemicarbazide (3b) were obtained by the addition of methyl or phenylisothiocyanates to 4-(benzoylamino) benzoyl hydrazine; then 5-(4-aminophenyl)-4- methyl-2,4 -dihydro-3H- l,2,4-triazolin-3-thione (4a) and 5-(4-aminophenyl)-4-p- henyl-2,4- dihydro-3H- 1,2,4-triazolin- 3-thione (4b) were gained with the cyclization of 3a or 3b with 2N sodium hydroxide. Finally, 4a and 4b reac ted with methyl, ethyl, allyl, cyclohexyl, phenyl, p.chlorophenyl and p.bro- mophenyl isothiocyanates and the following substances were prepared: N-methyl-N' -[4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-t- hion-5-yl) phenyl] thiourea (Va) N-allyl-N' -[4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-thi- on-5-yl) phenyl] thiourea (Vb) N-phenyl-N'- [4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-t- hion-S -yl) phenyl] thiourea (Vc) N-(p.bromophenyl)-N'-[4-[2-(p.bromophenylaminothiocarbonyl)- 4-methyl-2,4dihydro-3H- l,2,4-trazoline-3-thion-5-yl] phenyl] thioruea (Vd).67 ÖZET l,2,4-TriazoIin-3-tiyonlardan türeyen bazı tiyoüre bileşikleri üzerinde çalışmalar Bu çalışmada, l-[4-(benzoilamino) benzoil]-4-metil-tiyosemi kar- bazid (3a) ve l-[4-(benzoilamino) benzoil] -4-fenü-tiyosemikarbazid(3b), metil veya fenil izotiyosiyanatın 4-(benzoilamino) benzoilhidrazine katımı ile elde edilmiş; sonra 5-(4-aminofenil)-4-metil- 2,4-dihidro- 3H-1,2,4- tri- azolin- 3-tiyon (4a) ve 5-(4-aminofenil)- 4-fenil- 2,4-dihidro-3H- 1,2,4-tri- azolin-3-tiyon (4b), 3a veya 3b'nin 2N sodyum hidroksit ile siklizasyonu sonucu kazanılmışlardır. Son olarak, 4a ve 4b metil, etil, allil, siklohekzil, fenil, p.klorofenil ve p.bromofenil izotiyosiyanatlarla reaksiyona sokularak aşağıdaki maddeler hazırlanmıştır: N-metil-N' -[4-(4-metil-2,4- dihİdro- 3H-1.2.4- triazolin- 3-tiyon -5-il) fenil] tiyoüre (Va) N-allil-N' -[4-(4-metil-2,4-dihidro-3H- l,2,4-triazolin-3-tiyon-5- il) fenil] tiyoüre (Vb) N-fenil-N' -[4-(4-metil -2,4-dihidro- 3H- 1,2,4-triazoiin- 3-ti- yon-5 il) fenil] tiyoüre (Ve) N-(p.bromofenil)- N,-[4-[2-(p.bromofenilaminotiyokarbonil) -4- metil-2,4dihidro-3H- 1,2,4- triazolin- 3-tiyon-5-il] fenil] tiyoüre (Vd) N-metil-N'-[4-(4-fenil-2,4- dihidro-3H- 1,2,4-triazolin- 3-ti- yon-5-il) fenil] tiyoüre (Vf)

69 SUMMARY Studies on some thiourea derivatives obtained from l,2,4-triazoline-3-thiones In this study, l-[4-(benzoylamino) benzoyl]-4-methylthiosemicar- bazide (3a) and l-[4-(benzoylamino) benzoyl]-4-phenyl-thiosemicarbazide (3b) were obtained by the addition of methyl or phenylisothiocyanates to 4-(benzoylamino) benzoyl hydrazine; then 5-(4-aminophenyl)-4- methyl-2,4 -dihydro-3H- l,2,4-triazolin-3-thione (4a) and 5-(4-aminophenyl)-4-p- henyl-2,4- dihydro-3H- 1,2,4-triazolin- 3-thione (4b) were gained with the cyclization of 3a or 3b with 2N sodium hydroxide. Finally, 4a and 4b reac ted with methyl, ethyl, allyl, cyclohexyl, phenyl, p.chlorophenyl and p.bro- mophenyl isothiocyanates and the following substances were prepared: N-methyl-N' -[4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-t- hion-5-yl) phenyl] thiourea (Va) N-allyl-N' -[4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-thi- on-5-yl) phenyl] thiourea (Vb) N-phenyl-N'- [4-(4-methyl-2,4- dihydro-3H- l,2,4-triazoline-3-t- hion-S -yl) phenyl] thiourea (Vc) N-(p.bromophenyl)-N'-[4-[2-(p.bromophenylaminothiocarbonyl)- 4-methyl-2,4dihydro-3H- l,2,4-trazoline-3-thion-5-yl] phenyl] thioruea (Vd).67 ÖZET l,2,4-TriazoIin-3-tiyonlardan türeyen bazı tiyoüre bileşikleri üzerinde çalışmalar Bu çalışmada, l-[4-(benzoilamino) benzoil]-4-metil-tiyosemi kar- bazid (3a) ve l-[4-(benzoilamino) benzoil] -4-fenü-tiyosemikarbazid(3b), metil veya fenil izotiyosiyanatın 4-(benzoilamino) benzoilhidrazine katımı ile elde edilmiş; sonra 5-(4-aminofenil)-4-metil- 2,4-dihidro- 3H-1,2,4- tri- azolin- 3-tiyon (4a) ve 5-(4-aminofenil)- 4-fenil- 2,4-dihidro-3H- 1,2,4-tri- azolin-3-tiyon (4b), 3a veya 3b'nin 2N sodyum hidroksit ile siklizasyonu sonucu kazanılmışlardır. Son olarak, 4a ve 4b metil, etil, allil, siklohekzil, fenil, p.klorofenil ve p.bromofenil izotiyosiyanatlarla reaksiyona sokularak aşağıdaki maddeler hazırlanmıştır: N-metil-N' -[4-(4-metil-2,4- dihİdro- 3H-1.2.4- triazolin- 3-tiyon -5-il) fenil] tiyoüre (Va) N-allil-N' -[4-(4-metil-2,4-dihidro-3H- l,2,4-triazolin-3-tiyon-5- il) fenil] tiyoüre (Vb) N-fenil-N' -[4-(4-metil -2,4-dihidro- 3H- 1,2,4-triazoiin- 3-ti- yon-5 il) fenil] tiyoüre (Ve) N-(p.bromofenil)- N,-[4-[2-(p.bromofenilaminotiyokarbonil) -4- metil-2,4dihidro-3H- 1,2,4- triazolin- 3-tiyon-5-il] fenil] tiyoüre (Vd) N-metil-N'-[4-(4-fenil-2,4- dihidro-3H- 1,2,4-triazolin- 3-ti- yon-5-il) fenil] tiyoüre (Vf)