Off-campus UNL users: To download campus access dissertations, please use the following link to log into our proxy server with your NU ID and password. When you are done browsing please remember to return to this page and log out.

Non-UNL users: Please talk to your librarian about requesting this dissertation through interlibrary loan.

THE SYNTHESIS OF NEW 1,2,3-THIADIAZOLE DERIVATIVES

RONALD BRINTON PATTERSON, University of Nebraska - Lincoln

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

Share

COinS