Synthesis of Antimalarial Agents from 2,3-Dihydro-1,6-Diazaphenalene Derivatives.
Final rept. Oct 77-31 Dec 80,
WISCONSIN UNIV-MILWAUKEE DEPT OF CHEMISTRY
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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.