Mohammad salman Al-Ajely
Mosul University, Iraq
Title: Synthesis of some heterocyclic compounds derived from furfural
Biography
Biography: Mohammad salman Al-Ajely
Abstract
The present investigation includes the synthesis of number of 5,6 membered ring heterocyclic compounds containing one , two hetero atom such as pyrrole, thiazole , oxadiazole , thiadiazole. It include the Synthesis of 2-Methyl Sulfonyl-5-bromo-6-(2-phenyl amino)-1,3,4oxadiazole-5-yl-1,3-pyrimidine (E9) from the reaction of 5-methylisothiouriaSulfate(E2) with MBA to form the corresponding carboxylic acid (E3).This acid was then transformed into the corresponding hydrazide (E9) after a series of reaction processes. The resulting hydrazide was then reacted with isothiocyanate to yield the corresponding thiosemicarbazide (E8) .Cyclization of this compound using mercuric oxide lead to the formation of oxadiazole derivative (E9) , Synthesis of 2- Methyl sulfonyl -4- (N- formyl carbohydrazido) -5- bromo pyrimidine (E10) through the reaction of compound (E7) with formic acid, then cyclization of the product (E10) using phosphorous peta sulfide into thiadiazole (E11). This pathway was also includes the synthesis of carboxim –ido substituted pyrimidines (E15-E17) from the reaction of dimidone with (E12-E14) ,The resulting product was then allowed to react with compound (E4)to yield (E15-E17) compounds. The other part of this pathway include the synthesis of amidoxime (E18- E20) which then allowed to react with (E3) using DCC to form 2- methylthio -5-bromo-6-substituted amino oxmyl-1,3-pyrimidine-4- carboxylates( E21- E23) these carboxylates were cyclized by DMSO into 2- methyl thio -5- bromo-6-(3-substituted-1,2,4-oxadiazole-5-yl)-1,3-pyrimidine (E24-E26) , The work also include the synthesis of 3,4- dibromo crotono lactone -5-( substituted) carboxylate(E27-E29) from the reaction of MBA with either acetyl chloride , benzoyl chloride or nitro benzoyl chloride ,The compound (27) was then allowed to react with secondary aliphatic amines to form 5-(substituted amino)-3,4-dibromo crotono lactones(E30-E32). This pathway also includes the reaction of compound(28)with substituted anilines to give 4- (substituted anilino)-3-bromo-5-benzoyloxy crotono lactones(E33-E36).