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Phthalides and 1,3-indandiones. XVI. Preparation of 4-arylmethylenecinchomeronides and 2-aryl-5-aza-1,3-indandiones

P. Hrnčiar

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, Komenský University, Bratislava

 

Abstract: 4-Arylmethylenecinchomeronides were prepared by condensation of cinchomeronic acid anhydride with arylacetic acids. The yields of cinchomeronides and phtalides were compared. Pseudoesthers were obtained by addition of methanol and ethanol, respectively, to the cinchomeronides. On treatment with sodium methanolate in methylalcohol rearrangement occurs, 2-aryl-5-azaindan-l,3-diones being formed. 4-Arylacetylderivatives of nicotinic acid were prepared by hydrolysis of the cinchomeronides. 4-Phenyl - acetylnicotinic acid with diazomethane affords N-methylbetaine. N-Methyl-2-aryl-5-azaindan-1,3-dione betaines were prepared from 2-aryl-5-azaindan-1,3-diones with dime thy lsulphate.

Full paper in Portable Document Format: 195a360.pdf (in Slovak)

 

Chemical Papers 19 (5) 360–370 (1965)

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