ISOTHIAZOLES .3. CYCLOADDITIONS OF DIAZOALKANES TO 3-DIALKYLAMINOISOTHIAZOLE 1,1-DIOXIDES - COMPETITIVE RING-CLEAVAGE IN 3A,4-DIHYDRO-6AH-PYRAZOLO[3,4-D]ISOTHIAZOLE 1.1-DIOXIDES - FORMATION OF 2-THIA-3-AZABICYCLO[3.1.0]HEX-3-ENE 2,2-DIOXIDES AND OR PYRAZOLES/

Authors
CLERICI F FERRARIO T GELMI ML MARELLI R
Citation
F. Clerici et al., ISOTHIAZOLES .3. CYCLOADDITIONS OF DIAZOALKANES TO 3-DIALKYLAMINOISOTHIAZOLE 1,1-DIOXIDES - COMPETITIVE RING-CLEAVAGE IN 3A,4-DIHYDRO-6AH-PYRAZOLO[3,4-D]ISOTHIAZOLE 1.1-DIOXIDES - FORMATION OF 2-THIA-3-AZABICYCLO[3.1.0]HEX-3-ENE 2,2-DIOXIDES AND OR PYRAZOLES/, Journal of the Chemical Society. Perkin transactions. I, (18), 1994, pp. 2533-2536
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
18
Year of publication
1994
Pages
2533 - 2536
Database
ISI
SICI code
0300-922X(1994):18<2533:I.CODT>2.0.ZU;2-N
Abstract
3-Dialkylaminoisothiazole 1,1-dioxides 1 readily undergo cycloaddition s with diazoalkanes 2. The reaction is characterized by high site- and regio-selectivity. Cycloadducts 3 and 4 were found to undergo straigh tforward thermolysis reactions at elevated temperature through two dif ferent paths characterized respectively by loss of nitrogen or sulfur dioxide and diethylcyanamide. The different transformations affording pyrazoles 6 and derivatives of the new heterocycle 2-thia-3-azabicyclo [3.1.0]hex-3-ene 2,2-dioxide 5 are discussed.