The Chemistry of Phthalide-3-carboxylic Acid. V. The Reaction of the Acid With Imines

1989 ◽  
Vol 42 (1) ◽  
pp. 49 ◽  
Author(s):  
J Chiefari ◽  
WK Janowski ◽  
RH Prager
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Acetic Anhydride ◽  
Dimethyl Sulfoxide ◽  
Carboxylic Acids ◽  
Dehydration Product

Phthalide-3-carboxylic acids decarboxylate readily in the presence of imines, the product depending on the solvent used. In dimethyl sulfoxide, or in the absence of solvent, at 130�, the product is the 3-alkyl 3-hydroxyisoindolone or its dehydration product, but in acetic anhydride at 130� the product is a mixture of diastereoisomeric 3-acetylarninoalkylphthalides. The reactions can be applied to the synthesis of natural products such as the isoindoloisoquinoline and phthalideisoquinoline alkaloids.

scholarly journals Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers

2020 ◽  
Vol 11 (36) ◽  
pp. 10000-10004
Author(s):  
Faxiang Bu ◽  
Lijun Lu ◽  
Xia Hu ◽  
Shengchun Wang ◽  
Heng Zhang ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Oxidative Decarboxylation ◽  
Diaryl Ethers ◽  
Valuable Compounds

Carboxylic acid compounds are important chemicals and are widely present in various natural products. The conversion of carboxylic acids into valuable compounds is a promising field.

One Pot Conversion of Carboxylic Acid to Ketone Using Trimethylsilyl Chloride

2020 ◽  
Vol 07 ◽  
Author(s):  
Habtamu Gelaw Mekonnen ◽  
Samaresh Jana
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Organometallic Reagent ◽  
Trimethylsilyl Ester ◽  
Reaction Conditions ◽  
One Pot ◽  
Simple Process ◽  
Organolithium Reagents

Background: Ketone is abundant in many natural products and in pharmaceuticals. It is believed to be one of the important functional groups in organic chemistry. Till date,several research approaches have been made to access ketone from a readily available starting materials. One such notable transformation consists of the conversion of carboxylic acid to the corresponding ketone in a one pot manner. Objective: We aimed to develop a simple one pot reaction for the conversion of carboxylic acid to ketone. This reaction could be useful to convert all types of carboxylic acid to ketone in a facile manner. Methods: In this procedure, a carboxylic acid has been converted to the corresponding trimethylsilyl ester using trimethylsilyl chloride in the presence of a base. A suitable organometallic reagent can interact with the ester formed at 20°C to produce the corresponding ketone. Results: Under the optimized reaction conditions, various aromatic, aliphatic and heteroaromatic carboxylic acids have been converted to the corresponding ketones using organolithium reagents, in a one pot manner. Moderate to good yields of the desired ketones were observed in most of the transformations. Conclusion: Conversion of carboxylic acid to ketone has been reported in a one pot fashion, where carboxylic acid has been transformed to its silyl ester. Organolithium reagents were used as nucleophile for our reaction purpose, whereas the organomagnesium reagents were not useful for this transformation. Aliphatic, aromatic and heteroaromatic carboxylic acids have been converted to the ketones following a simple process.

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.

scholarly journals Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

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

THE TRANSMISSION OF POLAR EFFECTS: IV. THE KINETICS OF ESTERIFICATION WITH DIAZODIPHENYLMETHANE OF SUBSTITUTED HETEROCYCLIC CARBOXYLIC ACIDS

1966 ◽  
Vol 44 (13) ◽  
pp. 1493-1499 ◽  
Author(s):  
Keith Bowden ◽  
D. C. Parkin
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Rate Coefficients ◽  
Relative Ability ◽  
Indole Carboxylic Acid ◽  
Kinetics Of ◽  
Electron Effects

The rate coefficients for the reaction with diazodiphenylmethane, in ethanol at 30.0°, of a number of substituted indole-2-carboxylic acids, indole-3-carboxylic acids, coumarin-3-carboxylic acids, coumarilic acids, and N-phenylglycines have been determined. The effect of substitution is assessed by use of adapted Hammett and Dewar–Grisdale relations. The relations give good correlations for oxygen-ring heterocyclic systems, and the relative ability of the systems to transmit π-electron effects has been determined. An anomalous perturbing effect appears to operate in the indole-carboxylic acid systems.

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