Accession Number : AD0694307

Title :   1,2,4-TRIAZOLES AND 1,3,4-OXADIAZOLES FROM N-ACYLHYDRAZIDINES,

Corporate Author : BOEING SCIENTIFIC RESEARCH LABS SEATTLE WASH POLYMER SCIENCES LAB

Personal Author(s) : Hergenrother,Paul M. ; Pratt,Thomas J.

Report Date : AUG 1969

Pagination or Media Count : 20

Abstract : N-Acylhydrazidines were prepared from low temperature solution or interfacial condensation of hydrazidines (amidrazones) with carboxylic acid chlorides. The N-acylhydrazidines were quantitatively converted to the corresponding 1,3,4-oxadiazoles by heating in strong acids such as trifluoroacetic acid. Whereas, conversion of the precursor N-acylhydrazidines predominantly to the corresponding 1,2,4-triazoles was affected by refluxing in solvents such as m-cresol or by melt cyclocondensation at 250 to 300C. The 1,2,4-triazoles were contaminated with 0.8 to 3.6% of 1,3,4-oxadiazole. When the cyclodehydration of N-benzoyl-(2-pyridyl) hydrazidine was attempted by refluxing in acetic anhydride, the major component in the product was 3-(2-pyridyl)-5-methyl-1,2-4-triazole. (Author)

Descriptors :   (*NITROGEN HETEROCYCLIC COMPOUNDS, SYNTHESIS(CHEMISTRY)), (*PYRIDINES, CHEMICAL REACTIONS), CONDENSATION REACTIONS, OXYGEN HETEROCYCLIC COMPOUNDS

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE