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), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 23:4; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKALI METAL COMPOUNDS
AZINES
AZOLES
BOROHYDRIDES
BORON COMPOUNDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CONFORMATIONAL CHANGES
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DMSO
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
J-J COUPLING
KETONES
MULTIPLETS
NITROSO COMPOUNDS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POTASSIUM COMPOUNDS
REDUCTION
SODIUM COMPOUNDS
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SULFOXIDES
THIAZOLES
TRIAZINES
ULTRAVIOLET SPECTRA