Nucleophilic reactions at a Vinylic Center. XVII. formation of derivatives of 1,3,4-thiadiazole and 1,3,4-oxadiazole in the reaction of 2,2-dichlorovinyl Sulfones with thiosemicarbazide and Semicarbazide

Journal Article · Fri Aug 01 00:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6952844

Shainyan, B A; Indyukova, L N; Kalikmann, I D; Mirskova, A N

The reaction of 2,2-dichlorovinyl sulfones with thiosemicarbazide and semicarbazide, leading to the formation of 2-alkyl(aryl)sulfonylmethyl-5-amino-1,3,4-thiadiazoles and 2-alkyl(aryl)sulfonylmethyl-5-amino-1,3,4-oxadiazoles respectively, was investigated. In contrast, the reactions of sulfonylacetic esters with thiosemicarbazide and semicarbazide lead to the formation of 3-sulfonyl-methyl-5-mercapto-1,2,4-triazoles and 3-sulfonylmethyl-5-hydroxy-1,2,4-triazoles respectively. The derivatives of 1,3,4-thiadiazole and 1,3,4-oxadiazole are formed from the 2,2-dichlorovinyl sulfones by substitution of the two chlorine atoms with subsequent cyclization of the intermediately formed salts.

• Research Organization: Irkutsk Institute of Organic Chemistry, Siberian Branch
• OSTI ID: 6952844
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:3,PT.2; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
AZOLES
CARBONIC ACID DERIVATIVES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
DMSO
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
KINETICS
MASS SPECTRA
MELTING POINTS
MONOMERS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXADIAZOLES
PHYSICAL PROPERTIES
QUANTITY RATIO
REACTION KINETICS
SEMICARBAZIDES
SPECTRA
SULFONES
SULFOXIDES
SYNTHESIS
THERMODYNAMIC PROPERTIES
THIADIAZOLES
TRANSITION TEMPERATURE
VINYL MONOMERS
YIELDS