Abstract
The reactions of 1, 1, 3-trichloro-1-propene and also 1, 1, 1-trichloro-2-propene with acetoacetic ester gave α-(γ, γ-dichlorallyl)acetoacetic ester (I). In the reactions with aniline and o- and p-toluidines, the corresponding α-(γ, γ-dichloroallyl)-β-arylamino-crotonic esters were produced, thermal cyclization of which gave 2-methyl-3-(γ, γ-dichloroallyl)-4-hydroxyquinoline (II) and its 6CH3- (III) and 8CH3- (IV) homologs. With phosphorus oxychloride, II–IV gave the corresponding 4-chloro-substituted quinolines (V–VII); with concentrated sulfuric acid, II–VII were converted into the corresponding β-quinolinylpropionic acids VIII–XIII.
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For part XI, see [5].
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Gyul'budagyan, L.V., Chukhadzhyan, E.O. New derivatives of 4-quinaldinol. Chem Heterocycl Compd 4, 610–612 (1971). https://doi.org/10.1007/BF00481032
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DOI: https://doi.org/10.1007/BF00481032