Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Preparation of 3-Substituted Quinolines. I. Alkylation of Malonaldehyde Dianil Derivatives
REIKO TODORIKIMACHIKO ONOSHINZO TAMURA
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Keywords: cyclodehydration
JOURNAL FREE ACCESS

1983 Volume 31 Issue 12 Pages 4277-4285

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Abstract
2-Substituted 1-arylamino-3-arylimino-1-propenes (III) were prepared by the reaction of N-lithio derivatives of 1-arylamino-3-arylimino-1-propenes (malonaldehyde dianil derivatives) (II) and substituted benzyl bromides. 2-Allyl and 2-(2, 4-dinitrophenyl) derivatives of II were prepared by the same method. However, the alkylation failed with less reactive alkyl halides such as ethyl iodide as alkylating agents. Hydrolysis of III afforded α-substituted β-(arylamino) acroleins (IV), which afforded 3-substituted quinolines (V) on heating with aluminium chloride.
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© The Pharmaceutical Society of Japan
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