ORGANIC SULFUR COMPOUNDS III. CONDENSATIONS INVOLVING <i>o</i>-NITROBENZENESULFENYL CHLORIDE

Coutts, Ronald T.; Hindmarsh, K. W.; Pound, N. J.

doi:10.1139/v66-316

Can. J. Chem.

1966

DOI: 10.1139/v66-316

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ORGANIC SULFUR COMPOUNDS III. CONDENSATIONS INVOLVING o-NITROBENZENESULFENYL CHLORIDE

Ronald T. Coutts¹,

K. W. Hindmarsh²,

N. J. Pound³

Abstract: not available

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“…These properties are in contrast with those of the starting material 2a which was soluble in sodium hydroxide solution and showed no carbonyl stretching in the ir (5). Compound 2a presumably exists in the solid state as the en01 tautomer.…”

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Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

Coutts¹,

El-Hawari²,

Pound³

et al. 1976

Can. J. Chem.

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Can. J. Chem. 54, 993 (1976). Reduction of 3-methyl-4-(2-nitrophenylthio)-1-phenyl-2-pyrazolin-5-one (20) with sodium borohydride and palladium-charcoal gave two products which are identified as 3'-methyl-1'-phenylspiro[benzothiazoline-2,4'-[2]pyrazoline]-5'-one (3a) and 4-(2-mercaptopheny1amino)-3-methyl-I-phenyl-2-pyrazolin-5-one (4a). Evidence is presented in support of a reaction mechanism in which the spiro compound 3a is formed first and is then further reduced to the thiol 4a.Reduction of the 1,3-diphenyl-4-(2-nitrophenylthio)-2-pyrazolin-5-one (26) with the same reducing agent proceeded in a similar manner and diphenyl products 36 and 46, analogous to the spiro compound 3a and the thiol4a, respectively, were formed.Some chemical properties of the thiol 4a were investigated; it formed a dimethyl derivative, a diacetate, and a tribenzoate.Reduction of the pyrazolones 20 and 2b with zinc and ammonium chloride produced the same spirobenzothiazolines 30 and 36. RONALD T. COUTTS, ABDEL-MONAEM EL-HAWARI, NORMAN J. POUND et RUDOLPH A.ABRAMOVITCH. Can. J. Chem. 54, 993 (1976).La reduction de la methyl-3 (nitro-2 phenylthi0)-4 phenyl-l pyrazoline-2 one-5 (20) par le borohydrure de sodium et le palladium sur charbon conduit a deux produits que I'on a identifie comme etant la methyl-3' phenyl-I' spiro[benzothiazoline-2,A'-pyrazoline-2lone-5' (3a) et la (mercapto-2 phtny1amino)-4 methyl-3 phenyl-l pyrazoline-2 one-5 (4a). On presente des donnees qui supportent un mecanisme reactionnel dans lequel un compose de type spiro 3a est forme dans une premiere etape pour @tre ensuite reduit en thiol 40.La reduction de la diphenyl-1,3 (nitro-2 pheny1thio)-4 pyrazoline-2 one-5 (26) par le m&me agent reducteur conduit de la m&me maniere a d e w produits diphenyles 36 et 46 analogues respectivement au compose spiro 3a et au thiol4a.On a examine quelques proprietes chimiques du thiol 4a; il forme un derive dimtthylt, un diacetate et un tribenzoate.Le reduction des pyrazolones 20 et 2b par le zinc et le chlorure d'ammonium conduit aux m@mes spirobenzothiazolines 3a et 36.[Traduit par le journal]Palladium-charcoal catalyzed sodium borohydride reductions of cr-(0-nitrophenylthio) aliphatic acids (1) and esters (2,3) produce cyclic hydroxamic acids whichare formed via hydroxylamine intermediates. A similar reduction (4) of the pyrazolone l a yielded the corresponding hydroxylamine 16 as the major product, together with a small amount of the amine lc. It was of interest to us to extend these reduction studies to see whether catalyzed sodium borohydride reductions of the related pyrazolones 2a and 2b would produce cyclic N-hydroxylated 'For part 111, see ref. 17. products. Hydroxylamines, however, were not isolated; instead, the reaction followed an unexpected pathway.Pyrazolones 2a For personal use only.

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confidence: 58%

Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

Coutts¹,

El-Hawari²,

Pound³

et al. 1976

Can. J. Chem.

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p-Toluenesulphonic acid-promoted, I₂-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides

et al. 2014

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Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols

et al. 2016

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ORGANIC SULFUR COMPOUNDS III. CONDENSATIONS INVOLVING o-NITROBENZENESULFENYL CHLORIDE

Abstract: not available

Cited by 4 publications

References 1 publication

Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

p-Toluenesulphonic acid-promoted, I₂-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides

Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols

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ORGANIC SULFUR COMPOUNDS III. CONDENSATIONS INVOLVING o-NITROBENZENESULFENYL CHLORIDE

Abstract: not available

Cited by 4 publications

References 1 publication

Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

Derivatives of 2-pyrazolin-5-one. IV. Preparation and properties of two spiro[benzothiazoline-2,4′-[2]pyrazoline] derivatives

p-Toluenesulphonic acid-promoted, I2-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides

Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols

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Product

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p-Toluenesulphonic acid-promoted, I₂-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides