THE ORTON REARRANGEMENT IN APROTIC SOLVENTS: PART II. THE ACID-CATALYZED BROMINATION OF ANISOLE BY A SERIES OF 4-SUBSTITUTED N-BROMOACYLANILIDES

1965 ◽  
Vol 43 (4) ◽  
pp. 732-740 ◽  
Author(s):  
John M. W. Scott ◽  
June G. Martin
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Aprotic Solvents ◽  
Acid Catalyzed

Anisole has been brominated using a sequence of brominating reagents generated by the reaction of a series of 4-substituted N-bromoacylanilides 4-RC6H4NBrAc (R = Ph, H, Cl, and NO2) with a series of carboxylic acids R′COOH (R′ = CF3, CCl3, CH2Cl, and CH3). The isomer distributions of the bromoanisoles produced have been measured for each N-bromoacylanilide–carboxylic acid pair and their variation with both the structure of the N-bromoacylanilide and the carboxylic acid provides a useful basis for a discussion of the mechanism of the bromine migration.

THE ORTON REARRANGEMENT IN APROTIC SOLVENTS: III. THE ACID-CATALYZED CHLORINATION OF ANISOLE BY A SERIES OF 4-SUBSTITUTED N-CHLOROACYLANILIDES

1966 ◽  
Vol 44 (23) ◽  
pp. 2901-2907 ◽  
Author(s):  
John M. W. Scott ◽  
June G. Martin
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Transfer Reaction ◽  
Probable Mechanism ◽  
Aprotic Solvents ◽  
Acid Catalyzed ◽  
Reported Data

Anisole has been chlorinated with a sequence of chlorinating agents generated by the reaction of a series of 4-substituted N-chloroacylanilides (4-X-C6H4NClAc (X = Me, H, and CN)) with a series of carboxylic acids (R—COOH (R = CF3, CCl3, CH2Cl, and CH3)). The isomer ratios of the 2- and 4-chloroanisoles produced in these reactions have been measured for each N-chloroacylanilide – carboxylic acid pair, and are found to be dependent on the strength of the catalyzing acid but independent of the structure of the N-chloroacylanilide within the precision of the reported data. These observations are consistent with both the termolecular scheme proposed in part II of this series and the Soper mechanism. However, evidence derived from these and other observations suggests that the termolecular scheme is still the most probable mechanism for the chlorine transfer reaction.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

scholarly journals Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides

2006 ◽  
Vol 71 (2) ◽  
pp. 89-101 ◽  
Author(s):  
Sasa Drmanic ◽  
Bratislav Jovanovic ◽  
Aleksandar Marinkovic ◽  
Milica Misic-Vukovic
Keyword(s):  
Regression Analysis ◽  
Reaction Mechanism ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Rate Constants ◽  
Picolinic Acid ◽  
Correlation Coefficients ◽  
Aprotic Solvents ◽  
Pyridine Carboxylic ◽  
Similar Range

The rate constants for the reaction of three isomeric pyridine mono-carbocylic acid N-oxides with diazodiphenylmethane were determined at 30 ?C in thirty two protic and aprotic solvents by the well known UV spectrophotometric method. The rate constants are generally higher than for pyridine mono-carboxylic acids in a similar range of solvents, except for picolinic acid N-oxide, and also higher in protic than in aprotic solvents. The determined rate constants were correlated with solvent parameters using the Kamlet-Taft solvatochromic equation bymeans of multiple regression analysis. The sign of the equation coefficients were in agreement with the postulated reaction mechanism. The mode of the influences of the solvent is discussed on the basis of the correlation coefficients, taking into account the specific structures of the pyridine mono-carboxylic acid N-oxides.

Efficient and Regioselective Ring-opening of Epoxides with Carboxylic Acid Catalyzed by Graphite Oxide

2020 ◽  
Vol 17 (7) ◽  
pp. 532-538
Author(s):  
Maryam Mirza-Aghayan ◽  
Mahdieh Molaee Tavana ◽  
Elaheh Golam Alipour Niazi ◽  
Rabah Boukherroub
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Graphite Oxide ◽  
Ring Opening ◽  
Reaction Times ◽  
Metal Free ◽  
Ring Opening Reaction ◽  
Ring Opening Of Epoxides ◽  
Acid Catalyzed

An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleophile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

scholarly journals Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

2021 ◽  
pp. 174751982098715
Author(s):  
Khethobole C Sekgota ◽  
Michelle Isaacs ◽  
Heinrich C Hoppe ◽  
Ronnett Seldon ◽  
Digby F Warner ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Coupling Agent ◽  
Methyl Esters ◽  
Acid Anhydride

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids

2012 ◽  
Vol 67 (3-4) ◽  
pp. 123-128
Author(s):  
Anna Pachuta-Stec ◽  
Urszula Kosikowska ◽  
Anna Chodkowska ◽  
Monika Pitucha ◽  
Anna Malm ◽  
...  
Keyword(s):  
Biological Activity ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Condensation Reaction ◽  
Primary Amines ◽  
Pharmacological Activities

N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities

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