Issue 0, 1973

Cyclic amidines. Part XXV. Derivatives of 1-alkyl-2-aminoquinolin-4(1H)-ones and 2,3-dihydroimidazo[1,2-a]quinolin-5(1H)-one

Abstract

Interaction of ethyl cyanoacetate with N-alkylarylamine salts, yields 1-alkyl-2-aminoquinolin-4(1H)-ones. Alkylation of the aminoquinolinones yields O-alkyl derivatives which are strong bases. The same reagents cause alkylation first at O and then on ring N in 2-aminoquinolin-4-ols. 2-Ethoxycarbonylmethylene-1-phenylimidazolidine cyclises to 2,3-dihydroimidazo[1,2-a]quinolin-5(1H)-one, the 5-chloro-derivative of which reacts readily with alkylamines to yield 5-amino-derivatives; with acyl anhydrides and nitrous acid N-substituted derivatives are formed with replacement of Cl by O. The u.v.–visible spectra of the quinolines and imidazoquinolines are discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 1314-1320

Cyclic amidines. Part XXV. Derivatives of 1-alkyl-2-aminoquinolin-4(1H)-ones and 2,3-dihydroimidazo[1,2-a]quinolin-5(1H)-one

R. J. Grout, B. M. Hynam and M. W. Partridge, J. Chem. Soc., Perkin Trans. 1, 1973, 1314 DOI: 10.1039/P19730001314

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