Synthesis of 3-amino-4-hydroxylaminothiazolidine-2-thiones and 2,3-dimethyl-4. cap alpha. ,5-dihydro-7-thioxothiazolo(3,4-b)-1,2,4-triazines
The reaction of dimeric nitroso chlorides of olefins with potassium dithiocarbazate was used to synthesize 3-amino-4-hydroxylaminothiazolidine-2-thiones, which undergo rearrangement to 2-mercapto-1,3,4-thiadiazines on heating and react with butane-2,3-dione to give 2,3-dimethyl-4..cap alpha..,5-dihydro-7-thioxothiazolo(3,4-b)-1,2,4-triazine 4-oxides. The latter are reduced by sodium borohydride to the corresponding 3,4,4..cap alpha..,5-tetrahydro-7-thioxo derivatives. The IR spectra of KBr pellets of the compounds were recorded with a Perkin-Elmer spectrometer. The UV spectra of solutions in ethanol were obtained with a Specord UV spectrophotometer. The PMR spectra of solutions of the compounds in d/sub 6/-DMSO were obtained with a Varian FT-80A spectrometer with tetramethylsilane (TMS) as the internal standard.
- Research Organization:
- All-Union Scientific-Research Institute of Chemical Agents for the Protection of Plants, Moscow (USSR)
- OSTI ID:
- 6961586
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Vol. 23:4; Other Information: Translated from Khim. Geterotsikl. Soedin.; 23: No. 4, 554-556(Apr 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
KETONES
ISOMERIZATION
NMR SPECTRA
THIAZOLES
TRIAZINES
BOROHYDRIDES
CHEMICAL SHIFT
CONFORMATIONAL CHANGES
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DMSO
HYDROXY COMPOUNDS
INFRARED SPECTRA
J-J COUPLING
MULTIPLETS
NITROSO COMPOUNDS
POTASSIUM COMPOUNDS
REDUCTION
SODIUM COMPOUNDS
STRUCTURAL CHEMICAL ANALYSIS
ULTRAVIOLET SPECTRA
ALKALI METAL COMPOUNDS
AZINES
AZOLES
BORON COMPOUNDS
CHEMICAL REACTIONS
COUPLING
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
INTERMEDIATE COUPLING
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SPECTRA
SULFOXIDES
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory