Accession Number : ADA134269

Title :   Synthesis of Antimalarial Agents from 2,3-Dihydro-1,6-Diazaphenalene Derivatives.

Descriptive Note : Final rept. Oct 77-31 Dec 80,

Corporate Author : WISCONSIN UNIV-MILWAUKEE DEPT OF CHEMISTRY

Personal Author(s) : Cook,James M

PDF Url : ADA134269

Report Date : Apr 1982

Pagination or Media Count : 28

Abstract : The six step synthesis of the new imidazole-like heterocycle 1,6-diazaphenalene (8) from readily available cyclohexane-1,3-dione 1 and dimethyl beta-ketoglutarate 2 is described. In addition, a six step synthesis of 9-methoxy-diazaphenalene (34) from ethylacetoacetate and p-ansidine has also been accomplished. An investigation of the chemistry of 8 has been carried out and resulted in several routes to key 7-substituted-1,6-diazaphenalenes such as 10, 15, 16, and 17, as well as conditions under which to N-alkylate 8. In fact, this alkylation sequence has resulted in the preparation of the target 17. The reaction of 1,6-diazaphenalene with singlet oxygen and peracids has also been determined as well as preparation of several key derivatives in the 9-methoxy-series.

Descriptors :   *Antimalarials, *Quinolines, Synthesis(Chemistry), Molecular structure, Chemical reactions, Alkylation, Chemical analogs

Subject Categories : Pharmacology

Distribution Statement : APPROVED FOR PUBLIC RELEASE