Synthesis of 1, 2, 3-Triazole Compounds Derived from 4-Amino Benzoic Acid

F.Al-Smaisim, Rafah

	Synthesis of 1, 2, 3-Triazole Compounds Derived from 4-Amino Benzoic Acid
Al-Mustansiriyah Journal of Science
Article 1, Volume 21, Issue 5, 2010, Pages 291-302
Author
Rafah F.Al-Smaisim
Abstract
This work involves the synthesis of some 1,2,3-Triazoles derived from 4-aminobenzoic acid were synthesis 4-azido benzoic acid [1] synthesis by the action of sodium azide on the diazonium chloride salt, 4-(4-amino-5-cyano-1H-1,2,3-triazol-1-yl)benzoic acid [2] then 1-(4-carboxy-phenyl)-5-methyl-1-H-[1,2,3] triazole-4-carboxylic acid [3]by reaction of [1]with ethyacetoacetate and malonitrile; respectively in sodium ethoxide using absolute as a solvent. reaction of [2]with thionyl chloride to give acid chloride derivative [4], followed by conversion into the corresponding acid hydrazide derivative[5], carboxylic acid thiosemicarbazide [12], esters [15-17], thioesters [18], [19], and amides [20-22], when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry benzene; respectively. Then compound [5] reflux with various aldehydes and ketons to give a number of Schiff's bases [6-10]. Furthermore, 1,2,4-triazole derivative [13] have been also prepared by refluxing thiosemicarbazide derivative [12] with sodium hydroxide solution (4%) then acidify with (10%)HCl . Moreover, a thiadiazole derivative [14] has been prepared by treatment of thiosemicarbazide derivative [12] with concentrated sulfuric acid as cyclyzing agent. Finally, oxadiazole derivative [11] has prepared by condensation of its acid hydrazide derivative [5] with carbon disulfide in basic medium.

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