ORGANIC SULFUR COMPOUNDS: II. CATALYZED SODIUM BOROHYDRIDE REDUCTIONS OF SELECTED α-(o-NITROPHENYLTHIO) ACIDS

Autor:	R. T. Coutts, Elizabeth M. Smith, D. L. Barton
Rok vydání:	1966
Předmět:	Reducing agent Organic Chemistry chemistry.chemical_element General Chemistry Benzothiazine Medicinal chemistry Sulfur Catalysis Solvent chemistry.chemical_compound Sodium borohydride Acetic acid chemistry Hydrazobenzene Organic chemistry
Zdroj:	Canadian Journal of Chemistry. 44:1733-1741
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v66-262
Popis:	The products obtained when α-(o-nitrophenylthio) acids are reduced by means of sodium borohydride and palladium–charcoal depend on (a) the reaction temperature, (b) the solvent, (c) the length of time in which the α-(o-nitrophenylthio) acid is in contact with the reducing agent, and (d) the nature of the substituents on the α-(o-nitrophenylthio) acid. By varying these conditions, benzothiazine hydroxamic acids (i.e. substituted 3,4-dihydro-4-hydroxy-3-oxo-2H-1,4-benzothiazines), the corresponding lactams (3,4-dihydro-3-oxo-2H-1,4-benzothiazines), and derivatives of 2-carboxymethylthioazobenzene can be prepared.In two cases, additional products were obtained. When (o-nitrophenylthio)acetic acid was catalytically reduced for 30 min in dioxane, 3,4-dihydro-3-oxo-2H-1,4-benzothiazine-1,1-dioxide (VIc) was an unexpected product, and when α-(4-trifluoromethyl-2-nitrophenylthio)-isobutyric acid was left for a prolonged time in contact with sodium borohydride and palladium–charcoal, a derivative of hydrazobenzene, namely, 2-carboxy(α,α-dimethyl)methylthio-5-trifluoromethylhydrazobenzene (V), was one of the three identified products.
Databáze:	OpenAIRE
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