ChemInform Abstract: Selective Cleavage of Benzoxazoles (I) to o-Hydroxy N-Substituted Anilines (II) with Sodium Borohydride/Acetic Acid.

ChemInform ◽  
1990 ◽  
Vol 21 (30) ◽  
Author(s):  
B. YADAGIRI ◽  
J. W. LOWN
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Substituted Anilines

Bromination of 5a-lanost-8-en-3-one and 5a-lanost-8-ene-3,7,ll-trione

1982 ◽  
Vol 35 (4) ◽  
pp. 857
Author(s):  
J Collins ◽  
PS Cooper ◽  
RE Gall ◽  
A Georges
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Major Product ◽  
Equilibrium Conditions

Monobromination of 5α-lanost-8-en-3-one (la) under kinetic conditions gave exclusively the 2β- bromo ketone (3a) whilst under equilibrium conditions the product contained 85% of the 2α-bromo ketone (2a). Monobromination of 5a-lanost-8-ene-3,7,11-trione (1b) under kinetic conditions gave the 2a-bromo ketone (2b); 33% of the 2β-bromo ketone (3b) was formed under equilibrium conditions. The configuration assigned to the bromo ketones (2b) and (3b) has been confirmed by reduction with sodium borohydride and treatment of the derived bromohydrins (4b) and (6b) with base to give the 2β,3β-epoxide (5b) and the 3-ketone (1b) respectively. Cleavage of the 2β,3β(-epoxide (5a) with acetic acid gave 2α-acetoxy-5α-lanost-8-en-3β-ol (7) as the major product and 3α-acetoxy-5α-lanost- 8-en-2β-ol (a), in a boat like conformation, as the minor product.

scholarly journals Eine neue Methode zur Herstellung und Reinigung von 5-Methyltetrahydrofolsäure / A New Method for Preparation and Purification of 5-M ethyltetrahydrofolic Acid

1973 ◽  
Vol 28 (11-12) ◽  
pp. 650-652
Author(s):  
Harold Rüdiger ◽  
Reinhard Siede
Keyword(s):  
Acetic Acid ◽  
Folic Acid ◽  
Ion Exchange ◽  
Sodium Borohydride ◽  
Sodium Salt ◽  
Barium Salt ◽  
Borohydride Reduction ◽  
Methyl Derivative ◽  
Crude Product ◽  
Sodium Borohydride Reduction

Abstract 5-Methyltetrahydrofolic acid is prepared from folic acid by sodium borohydride reduction, reac­ tion with formaldehyde and reduction to the methyl derivative by sodium borohydride. The crude product is precipitated as barium salt which after having been converted to the sodium salt by ion exchange is adsorbed to QAE-Sephadex and eluted by different acetic acid gradients in subsequent chromatographies. This method allows to process gram quantities on reasonably small columns

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

Reactions of N-substituted 2-aminopyridines with chloroacetyl chloride; Formation of a new series of heterocyclic betaines: 1-Substituted 4-chloromethyl-2-oxopyrido[1,2-a]pyrimidin-5-ium-3-olates

1989 ◽  
Vol 54 (5) ◽  
pp. 1376-1387 ◽  
Author(s):  
Hana Hulinská ◽  
Miloš Buděšínský ◽  
Jiří Holubek ◽  
Oluše Matoušová ◽  
Hana Frycová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Nmr Spectra ◽  
Aqueous Ethanol ◽  
Hydrogen Bromide ◽  
Chloroacetyl Chloride ◽  
Gastric Lesions ◽  
Substitution Reactions ◽  
Reaction Compound ◽  
C Nmr

N-(2-Pyridyl)-2-chloroacetamide reacted with 1-methylpiperazine and gave the expected compound III. Attempts at preparing the N-substituted N-(2-pyridyl)-2-chloroacetamides by reactions of N-substituted 2-aminopyridines with chloroacetyl chloride in benzene in the presence of N,N-dimethylacetamide were negative and took an unexpected course. 2-Anilinopyridine and 2-(cyclohexylamino)pyridine afforded compounds which were identified by 1H and 13C NMR spectra as the heterocyclic betaines IVa and IVb. 2-(1-Butylamino)pyridine, 2-(benzylamino)pyridine and 2-(2-phenylethylamino)pyridine gave similarly compounds IVc-IVe. The chloromethyl compounds IVa-IVe underwent normal substitution reactions with 1-methylpiperazine and gave the methylpiperazino compounds Va-Ve. Attempts to reduce the betaines with sodium borohydride in aqueous ethanol proceeded in one case as the hydrogenolytic displacement of the chlorine atom with hydrogen (product VIa), in another case as ethanolysis (product VIIb). Formation of VIb by treatment of IVb with hydrogen bromide in boiling acetic acid is probably the result of a disproportionation reaction. Compound III (dimaleate VÚFB-17 103) was practically equipotent with pirenzepine (I) as an anti-ulcer agent in the test of indomethacine-induced gastric lesions in rats but was much weaker in tests for antocholinergic and antisecretory activity.

THE PREPARATION OF 9-HYDROXYPYRAZOLO[3,4-b]QUINOLINES

1966 ◽  
Vol 44 (17) ◽  
pp. 2009-2014 ◽  
Author(s):  
R. T. Coutts ◽  
J. B. Edwards
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Sodium Borohydride ◽  
Sodium Acetate ◽  
The Other ◽  
Reduction Product ◽  
Type I

4-(2-Nitrobenzylidene)-2-pyrazolin-5-ones (I) were best prepared by heating o-nitrobenzaldehyde and 2-pyrazolin-5-ones in acetic anhydride containing fused sodium acetate (cf. Erlenmeyer azlactone synthesis). Pyrazolones of type I were reductively cyclized with cyclohexene and palladium–charcoal, and gave 3a,4,9,9a-tetrahydro-9-hydroxy-1H-pyrazolo-[3,4-b]quinolines (II) which, as expected, were amphoteric compounds. Of the three other methods of reduction used in this study, two (zinc and acetic acid; sodium borohydride and palladium–charcoal) were capable of producing pyrazoloquinolines, but were less reliable. The other method employed (hydrazine hydrate and palladium–charcoal) caused degradation of the pyrazolone molecule in the two cases examined, and in both, bis(2-aminobenzylidene) hydrazine (V) was the reduction product isolated.

scholarly journals Meso-tetraphenylporphyriniron(iii) chloride catalyzed oxidation of aniline and its substituents by magnesium monoperoxyphthalate in aqueous acetic acid medium

2012 ◽  
Vol 14 (4) ◽  
pp. 35-41 ◽  
Author(s):  
Raja Manickam ◽  
Karunakaran Kulandaivelu
Keyword(s):  
Acetic Acid ◽  
Acid Medium ◽  
First Generation ◽  
Activation Parameters ◽  
Aqueous Acetic Acid ◽  
Substituted Anilines ◽  
Isokinetic Relationship ◽  
Acetic Acid Medium ◽  
Linear Free Energy ◽  
Energy Relationships

Abstract The catalytic properties of the first generation catalyst meso-tetraphenylporphyriniron(III) chloride and magnesium monoperoxyphthalate (MMPP) as oxidant have been studied in the oxidation of aniline and its substituents in acetic acid medium. The thermodynamic parameters for the oxidation have been determined and discussed. It confirms the Exner relationship (only at the low range of temperatures) and also some of the activation parameters to the isokinetic relationships. The magnesium monoperoxyphthalate oxidation with 18 ortho- meta- and para-substituted anilines fulfills with isokinetic relationship but not to any of the linear free energy relationships. The reaction mechanism and the rate law were proposed.

Heterocyclic compounds from alloxan and amines. XI. Uramils, dialuric acids, and related compounds

1970 ◽  
Vol 23 (6) ◽  
pp. 1229 ◽  
Author(s):  
JW Clark-Lewis ◽  
K Moody
Keyword(s):  
Acetic Acid ◽  
Anthranilic Acid ◽  
Heterocyclic Compounds ◽  
Aqueous Ethanol ◽  
Substituted Anilines ◽  
Pyrimidine Derivatives ◽  
Ring Contraction ◽  
Related Compounds

Preparation of a number of uramils and 5-aryldialuric acids from o-substituted anilines is described. Methylation of the uramils gave dimethoxy-N-monomethyl pyrimidine derivatives accompanied by minor amounts of trimethoxy-pyrimidines, and the dialuric acids gave 1,3-dimethylpyrimidines or 5-methoxy-1,3-dimethylbarbituric acids (with an excess of diazomethane). Ring contraction of the 1,3-dimethyldialuric acids gave the isomeric 5-N-methylcarbamoyloxazolidine-2,4-diones. The dialuric acid from dimedone gave a trimethyl derivative (a methoxycyclohexenyl-1,3-dimethyldialuric acid). Anthranilic acid and alloxan in acetic acid gave a benzoxazonespirobarbituric acid, but in aqueous ethanol yielded a dialuric acid which was characterized by conversion into several derivatives. Infrared and N.M.R. data are recorded for the uramils, dialuric acids, and their derivatives.

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