Cyclic amidines. Part XXV. Derivatives of 1-alkyl-2-aminoquinolin-4(1H)-ones and 2,3-dihydroimidazo[1,2-a]quinolin-5(1H)-one
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1314-1320
- https://doi.org/10.1039/p19730001314
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.Keywords
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