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THE SYNTHESIS OF NEW 1,2,3-THIADIAZOLE DERIVATIVES
Abstract
The reactions of 1,2,3-thiadiazole-4-carbonyl chloride with the appropriate amines led to formation of the following amides in good yield: N-ethyl-1,2,3-thiadia- zole-4-carboxamide; N-methyl-1,2,3-thiadiazole-4-carbox- amide; N-cyclohexyl-1,2,3-thiadiazole-4-carboxamide; N- hexyl-1,2,3-thiadiazole-4-carboxamide; 4-(1,2,3-thiadia- zol-4-ylcarbonyl) morpholine; N,N-diphenyl-1,2,3-thiadia- zole-4-carboxamide; N-(B-naphthyl)-1,2,3-thiadiazole-4- carboxamide; N-(4-methyl-21,6'-dibromophenyl)-1,2,3-thi- adiazole-4-carboxamide; and N-(3-methyl-2-pyridyl)-1,2,3- thiadiazole-4-carboxamide. These compounds were characterized by their infrared and NMR spectra, as well as elemental analyses.4-Diazoacetyl-1,2,3-thiadiazole was prepared from the acid chloride and diazomethane in good yield and subjected to the Arndt-Eistert synthesis. The thiadiazole ring decomposed to unidentified products under these reaction conditions.The Land reaction was employed to synthesise -aco- tyl-1,2,3-thiadiazole in fair yield. The reaction of the methyl ketone and thiosemicarbaside gave a high yield of scetyl-1,2,3-thiadiazole thiosemicarbazone. The method of Hurd and Mori was employed to prepare 4,4'-bi-1,2,3- thiadiazolyl using 4-acetyl-1,2,3-thiadiazole as the star- ting material. Their method was also employed to prepare the bl-ring compound starting from 2,3-butanedione. The attemted Willgewrodt-Kindler synthesia with -acetyl- 1,2,3-thiadiazole led to decomposition products, one of which was postulated as thiesucoinie bis-morpholide. Prolonged heating at reflux of h-acetyl-1,2,3-thiadiazole in morpholine cave two decomposition products, of which one was identified as thioscetomorpholide.N-[2-D1aso-3-oxo-3-(1,2,3-thiadiazolyl)propionyl]- glycine ethyl ester was prepared from the acid chloride and -(diazoacetyl) glycine ethyl ester.The method of Hard and Mori was employed to prepare ethyl-1,2,3-thiadiazole-5-carboglycine ethyl ester uning -(acetoacetyl) glycine athyl ester as the starting material.A previously described method employing the Wolff diana synthesis was used to prepare 4,5-bi-1,2,3-thissolyl. The attempted formation of a Diels-Alder adduct with leic anhydride led to almost quantitative recovery of the thiadiazole starting material.
Subject Area
Organic chemistry
Recommended Citation
PATTERSON, RONALD BRINTON, "THE SYNTHESIS OF NEW 1,2,3-THIADIAZOLE DERIVATIVES" (1970). ETD collection for University of Nebraska-Lincoln. AAI7017744.
https://digitalcommons.unl.edu/dissertations/AAI7017744