Accession Number : AD0724173

Title :   Synthesis of Certain Benzoquinoline Derivatives.

Descriptive Note : Rept. no. 2 (Final), 1 Sep 66-31 May 68,

Corporate Author : IOWA UNIV IOWA CITY

Personal Author(s) : Gannon,Joseph G.

Report Date : FEB 1971

Pagination or Media Count : 45

Abstract : As a part of the antimalarial program, a series of quinolinemethanols based upon dimethoxylated 2-phenylbenzo(h)quinoline systems was prepared. The Doebner pyruvic acid synthesis was utilized for the annelation step leading to benzo(h)cinchoninic acids, which were further elaborated at the carboxyl group by literature procedures to the desired quinolinemethanols. In work leading to the linearly annelated benzo(g)quinolinemethanols, a number of highly substituted 2-naphthylamines was prepared. Attempts to employ these in Doebner pyruvic acid syntheses failed completely. No reason for these failures could be determined. It was found that these 2-naphthylamines undergo normal Combes cyclization reactions, to form linear benzo(g)quinoline systems, and that they also undergo the Knorr reaction, giving rise either to benzo(g)quinolines or to the isomeric angularly annelated benzo(f)- system. (Author)

Descriptors :   (*QUINOLINES, SYNTHESIS(CHEMISTRY)), (*ANTIMALARIALS, QUINOLINES), AMINES, CARBINOLS, POLYCYCLIC COMPOUNDS, CARBOXYLIC ACIDS

Subject Categories : Pharmacology
      Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE