Nucleophilic substitution without neighbouring acyloxy-group participation. Reaction of acylglycerols with the reagent system triphenylphosphine–diethyl azodicarboxylate–carboxylic acid

1974 ◽  
pp. 963-964 ◽  
Author(s):  
Rajindra Aneja ◽  
Alan P. Davies ◽  
Alexander Harkes ◽  
Jefferey A. Knaggs
Keyword(s):  
Carboxylic Acid ◽  
Nucleophilic Substitution ◽  
Group Participation ◽  
Diethyl Azodicarboxylate ◽  
Acyloxy Group

scholarly journals Development of variously functionalized nitrile oxides

2015 ◽  
Vol 11 ◽  
pp. 1241-1245 ◽  
Author(s):  
Haruyasu Asahara ◽  
Keita Arikiyo ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Carboxylic Acid ◽  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Grignard Reagent ◽  
Cycloaddition Reaction ◽  
Chemical Transformations ◽  
Nitrile Oxides ◽  
Weinreb Amide ◽  
Isoxazole Derivatives ◽  
Acid Esters

N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole derivatives. Since the amide was prepared by the cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide, the nitrile oxide served as the equivalent of the nitrile oxides bearing a variety of functional groups such as carboxy, alkoxycarbonyl, carbamoyl, acyl and formyl moieties.

Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives

2009 ◽  
Vol 63 (5) ◽  
Author(s):  
Ivana Bradiaková ◽  
Tatiana Ďurčeková ◽  
Naďa Prónayová ◽  
Anton Gatial ◽  
Alžbeta Krutošíková
Keyword(s):  
Carboxylic Acid ◽  
Nucleophilic Substitution ◽  
Chlorine Atom ◽  
Methyl Iodide ◽  
Secondary Amines ◽  
Pyridine Derivatives ◽  
Hydrolysis Of

Abstract2-[3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (I) was prepared by a three-step synthesis. Its reaction with phosphorus sulfide rendered thione II which was methylated to 2-[3-(Trifluoromethyl)phenyl]-4-methylsulfanylfuro[3,2-c]pyridine (III). 5-Methyl-2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (IV) was obtained by the reaction of I with methyl iodide in PTC conditions. The chlorine atom in derivate V was replaced with heterocyclic secondary amines via nucleophilic substitution and 4-substituted furopyridines VIa and VIb were thus prepared. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va.

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