Ivanov reagent


This procedure is an adaption of one described by Hauser and Chambers. Previous preparations include the benzylation of diethyl phenylmalonate followed by hydrolysis, the benzylation of phenylacetonitrile followed by hydrolysis, the benzylation of phenylacetic acid through the Ivanov reagent, and the reduction of oi-phenylcinnamic acid using sodium amalgam.  [c.40]

Treatment of the sodium salt of phenylacetic acid with iso-propylmagnesium bromide affords the so-called Ivanov reagent, a formally doubly charged species whose anionic moiety is often formulated as 56. This dianion undergoes aldol condensation with cyclopentanone to give the corresponding hydroxyacid (57). Alkylation of the salt of the acid with w-C2-chloroethyl)dimethylamine gives cyclopentolate (58).This agent has atropine-like activity with the midriatic component predominating.  [c.92]

Modification of the Erlenmeyer reaction has been developed using imines of the carbonyl compounds, obtained with aniline," benzylamine or n-butylamine. Ivanova has also shown that an A-methylketimine is an effective reagent in the Erlenmeyer azlactone synthesis. Quantitative yield of 19 is generated by treatment of 3 equivalents of 2-phenyl-5(4ff)-oxazolone (2) (freshly prepared in benzene) with 1 equivalent of iV-methyl-diphenylmethanimine (18) in benzene. Products resulting from aminolysis (20), alkali-catalyzed hydrolysis (21), and alcoholysis (22) were also described.  [c.231]


The organic chemistry of drug synthesis Vol.1 (1977) -- [ c.92 , c.93 ]