Synthesis of Certain Benzoquinoline Derivatives.
Rept. no. 2 (Final), 1 Sep 66-31 May 68,
IOWA UNIV IOWA CITY
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As a part of the antimalarial program, a series of quinolinemethanols based upon dimethoxylated 2-phenylbenzohquinoline systems was prepared. The Doebner pyruvic acid synthesis was utilized for the annelation step leading to benzohcinchoninic acids, which were further elaborated at the carboxyl group by literature procedures to the desired quinolinemethanols. In work leading to the linearly annelated benzogquinolinemethanols, 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 benzogquinoline systems, and that they also undergo the Knorr reaction, giving rise either to benzogquinolines or to the isomeric angularly annelated benzof- system. Author
- Organic Chemistry