1, 2, 4-triazin-5(4H)-on bileşiklerinin sübstitüsyon reaksiyonlarının incelenmesi

Abstract

Bu çal mada ba lang ç maddesi olarak glioksilik asit monohidrat ve tiyokarbohidrazidinreaksiyonu ile 4-Amino 3-merkapto-1,2,4-triazin -5(4H)-on bile i&i elde edildi. 4-Amino 3-merkapto-1,2,4-triazin -5(4H)-on'nun metil iyodür ile reaksiyonundan 4-Amino-3-metiltiyo-1,2,4-triazin-5(4H)-on bile i&i sentezlendi.Heptil bromür ,Oktil bromür,1,3-Dibrom propan ve 1,11-dibrom undekan ile 4-Amino-3-merkapto-1,2,4-triazin -5(4H)-on `nun SH grubundaki sübstitüsyon reaksiyonu ile yeni 4-Amino-3-heptiltiyo-1,2,4-triazin-5(4H)-on, 4-Amino-3-oktiltiyo-1,2,4-triazin-5(4H)-on,Bis(5-okso-4-amino-4H-1,2,4-triazin-3-il)-1,3-ditiyopropan ve Bis-(5-okso-4-amino-4H-1,2,4-triazin-3-il)-1,11-ditiyoundekan bile ikleri elde edildi.3,3'-Tiyodipropiyonik asit vedodekandioik asit kullan larak 4-Amino-3-merkapto -1,2,4-triazin -5(4H)-on `nun SH veNH2 gruplar n içine alan halka kapanmas reaksiyonu ile yeni 2,2'-Tiyobis{4-okso-4H-1,3,4-tiyadiazolo[2,3-c][1,2,4]-triazin-7-etil}ve 1,10-Bis(4-okso-4H-[1,3,4]tiyadiazolo[2,3 c][1,2,4] triazin -7-il)dekan bile ikleri sentezlendi.p-Dimetilamino benzaldehit ve 5-Bromosalisilaldehit ile 4-Amino- 3-merkapto-1,2,4-triazin-5(4H)-on' nun reaksiyonu ile 4-[4-(Dimetilamino) benzilidenimino-3-merkapto-1,2,4-triazin-5(4H)-on ve 4-(5-Bromosalisilidenimino)-3-merkapto-1,2,4-triazin-5(4H)-on bile ikleri sentezlendi.Elde edilen bu 8 adet yeni bile ik kristalizasyon ve kromatografik yöntemler ilesafla t r ld .Yap lar elementel analiz, IR ve 1H-NMR spektrumlar yard m ile ayd nlat ld .1

The first step of this work was to obtain 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one fromthe reaction of glioxylic acid monohydrate with thiocarbohydrazide. 4-amino-3-methylthio-1,2,4-triazin-5(4H)-one was obtained from the reaction of 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one with methyl iodide.4-amino-3-heptylthio-1,2,4-triazin-5(4H)-one, 4-amino-3-octylthio-1,2,4-triazin-5(4H)-one,Bis(5-oxo-4-amino-4H-1,2,4-triazin-3-il)-1,3-dithiopropane and Bis(5-oxo-4-amino-4H-1,2,4-triazin-3-il)-1,11-dithioundecan was obtained as a result of the substition reactions of 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one with heptyl bromide, octyl bromide, 1,3-dibromopropane and 1,11-dibromide undecan. Cyclizations of acids including SH and NH2 groupssuch as 3,3?-thiodipropiyonic acid and dodecanedioic acid having dicarboxyl groups with 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one gave 2,2?-thiobis{4-oxo-4H-1,3,4-thiadiazolo[2,3-c][1,2,4]-triazine-7-ethyl}and 1,10-bis(4-oxo-4H-[1,3,4]thiadiazolo[2,3 c][1,2,4]triazin-7-yl)decane, respectively.Using aldehydes such as p-dimethylaminobenzaldehyde and 5-bromosalicylaldehyde with 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one yielded the corresponding Schiff bases, 4-[4-(dimetilamino)benzylideneimino]-3-mercapto-1,2,4-triazin-5(4H)-one and 4-(5-bromosalicylideneimino)-3-mercapto-1,2,4-triazin-5(4H)-one, respectively.Eight novel compounds were purificated by crystallization and chromatographic methods andtheir structures were determined by elemental analysis, IR and 1H-NMR spectra.1