Reduction of 3-Acyl Derivatives of Oxindoles, Benzo[b]furan-2-ones, and Benzo[b]thiophen-2-ones to the Corresponding Alkyl Derivatives by Sodium Borohydride—Acetic Acid.

ChemInform ◽  
2006 ◽  
Vol 37 (35) ◽  
Author(s):  
Francis X. Smith ◽  
Brian D. Williams ◽  
Eric Gelsleichter ◽  
Judy A. Podcasy ◽  
John T. Sisko ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Alkyl Derivatives ◽  
Derivatives Of ◽  
Acyl Derivatives

Reduction of 3‐Acyl Derivatives of Oxindoles, Benzo[b]furan‐2‐ones, and Benzo[b]thiophen‐2‐ones to the Corresponding Alkyl Derivatives by Sodium Borohydride–Acetic Acid

2006 ◽  
Vol 36 (6) ◽  
pp. 765-769 ◽  
Author(s):  
Francis X. Smith ◽  
Brian D. Williams ◽  
Eric Gelsleichter ◽  
Judy A. Podcasy ◽  
John T. Sisko ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Alkyl Derivatives ◽  
Derivatives Of ◽  
Acyl Derivatives

scholarly journals CHEMISTRY AND SYNTHESIS OF SOME DIHYDRO-2H-l,4-BENZOTHIAZINE DERIVATIVES

1966 ◽  
Vol 44 (11) ◽  
pp. 1247-1258 ◽  
Author(s):  
Raj Nandan Prasad ◽  
Karin Tietje
Keyword(s):  
Alkyl Halides ◽  
Reduction Product ◽  
Alkyl Derivatives ◽  
Reaction Proceeds ◽  
Thiazine Ring ◽  
Derivatives Of ◽  
Compound Xviii ◽  
Acyl Derivatives

The formation of 3-oxo-3,4-dihydro-2H-1,4-benzothiazine (IIIa) by cyclization of alkyl 2-haloacetamidophenyl sulfides (I) was investigated; it is proposed that the reaction proceeds via a six-membered sulfonium halide. The preparation of 4-alkyl derivatives of IIIa and of 4-alkyl and 4-acyl derivatives of its reduction product 3,4-dihydro-2H-1,4-benzothiazine (Va) is described. Acylation of Va was shown to proceed without opening of the thiazine ring. Preparation of the O-benzoyl, N-benzoyl, and O,N-dibenzoyl derivatives of 2-(β-hydroxyethyl-mercapto)aniline (VIII) has permitted clarification of the confusion in the literature with respect to the derivatives of Va and VIII. Compound XVIII, the 1,1-dioxide of IIIa, undergoes C-alkylation at the 2-position when treated with alkyl halides, rather than O-alkylation as previously suggested.

8-Substitution derivatives of D-6-methylergoline-I

1983 ◽  
Vol 48 (1) ◽  
pp. 312-318 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Jiří Holubek ◽  
Jiří Roubík
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Dimethyl Sulphoxide ◽  
Quinoxaline Derivative ◽  
Derivatives Of ◽  
Dihydroxy Derivative

Reactions of esters I and II with methylsulphinylmethylsodium in dimethyl sulphoxide afforded β-keto sulphoxides III and IV, which were converted either into compounds V and VI under the conditions of the Pummerer rearrangement, or into ketones VII and VIII by the action of aluminium amalgam in 1,2-dimethoxyethane. Reduction of the compounds III and V with sodium borohydride produced β-hydroxy sulphoxide IX and dihydroxy derivative X respectively; the latter was characterised in the form of derivatives XI and XII. Condensation of the compound III with 1,2-diaminobenzene in acetic acid gave quinoxaline derivative XIII. The compounds prepared had no marked antilactation or antinidation activity.

REACTIONS OF NITRO SUGARS: I. SOME BENZYLIDENE AND ACYL DERIVATIVES OF METHYL 3-DEOXY-3-NITRO-D-HEXOPYRANOSIDES

1965 ◽  
Vol 43 (6) ◽  
pp. 1829-1834 ◽  
Author(s):  
Hans Helmut Baer ◽  
Frank Kienzle ◽  
Thomas Neilson
Keyword(s):  
Acetic Acid ◽  
Reaction Conditions ◽  
Derivatives Of ◽  
Acyl Derivatives

The 4,6-O-benzylidene derivatives VII, VIII, and XVII of methyl 3-deoxy-3-nitro-β-D-mannopyranoside, -β-D-galactopyranoside, and -α-D-glucopyranoside, respectively, were prepared. Acetylation of the β-D-manno derivative (VII) led, depending upon the reaction conditions, to its 2-O-acetate (IX) and, by way of an unexpected epimerization, to the 2-O-acetate (V) of the corresponding β-D-gluco isomer. There is evidence that this epimerization proceeds through methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-erythro-hexopyranos-2-enide (VI). This nitroolefin was obtained by a Schmidt–Rutz reaction from IX (as earlier from V) and was shown to add acetic acid readily giving V. It also added ethanol producing a 2-O-ethyl glycoside (XII). Acetylation of the galacto derivative (VIII) did not afford an acetate but proceeded with dehydration yielding methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-thero-hexopyranos-2-enide (X).A number of further derivatives of methyl 3-deoxy-3-nitro-β-D-glucopyranoside were prepared, viz., the 2-O-acetyl (XI), 2-deoxy-6-O-tosyl (XIV), and 2,6-dideoxy-6-iodo (XV) derivatives.

Derivatives of 2-pyrazolin-5-one. V. Preparation and properties of 1′,2′-dihydrospiro[[2]pyrazoline-4,3′ (4′H)-quinoline]-5-one.derivatives and related compounds

1977 ◽  
Vol 55 (15) ◽  
pp. 2856-2866 ◽  
Author(s):  
Ronald T. Coutts ◽  
Abdel-Monaem El-Hawari
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Lithium Aluminum Hydride ◽  
Catalytic Reduction ◽  
Aluminum Hydride ◽  
Spiro Compounds ◽  
Lithium Aluminum ◽  
Aldehydes And Ketones ◽  
Derivatives Of ◽  
Related Compounds

1′,2′-Dihydro-3-methyl-1-phenylspiro[[2]pyrazoline-4,3′(4′H)-quinoline]-5-one (8q), the structurally related 1,3-diphenylspiro[pyrazolone-quinoline] 8r and numerous 2′-substituted derivatives of 8q and 8r are readily accessible from catalytic reduction of 3-methyl-1-phenyl- or 1,3-diphenyl-4-(2-nitrobenzyl)-2-pyrazolin-5-one (1a, 1b, respectively) in alcohols (with the incorporation of the alkylidene moiety) or by interaction of the corresponding 2-aminobenzyl precursors (3a, 3b) with appropriate aldehydes and ketones. All spiro compounds were characterized by mass, ir, and 1Hmr spectra. The products obtained by reducing the spiro compounds with sodium borohydride and with lithium aluminum hydride are described. Reduction of 1a and 1b with zinc and acetic acid gave 3-methyl-1-phenyl- and 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline (2a, 2b, respectively).

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

1966 ◽  
Vol 44 (15) ◽  
pp. 1733-1741 ◽  
Author(s):  
R. T. Coutts ◽  
D. L. Barton ◽  
Elizabeth M. Smith
Keyword(s):  
Acetic Acid ◽  
Reaction Temperature ◽  
Sodium Borohydride ◽  
Hydroxamic Acids ◽  
Isobutyric Acid ◽  
Sulfur Compounds ◽  
Reducing Agent ◽  
Organic Sulfur Compounds ◽  
Unexpected Product ◽  
Derivatives Of

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.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

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