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), Vol. 22:3,PT.2
• Country of Publication: United States
• Language: English

Related Subjects

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