Synthesis of Antimalarial Agents from 2,3-Dihydro-1,6-Diazaphenalene Derivatives.
Abstract
The nitration of 1,6-diazaphenalene 1 has been difficult for the major product resulted from nitration of both positions -3 and -7 of 1, however, the problem of mononitration has been solved by the use of a NaNO2/CF3CO2H nitration mixture at -63 C. This procedure gave the desired mononitro compound 17 in 40% yield and some unreacted starting material. Because of the earlier difficulty with mononitration of 1,6-diazaphenalene, a new procedure was required to functionalize the 9-methoxy-1,6-diazaphenalene analogs. This set-back has been overcome by stirring either 4-methyl-5-amino 6-methoxyquinoline or 1,6-diazaphenalene 1 with phenyldiazonium chloride to provide the 5,8-diamino-compound 25 or the 7-functionalized diazaphenalene 19, respectively. It is planned to use this technology to incorporate an amine function into position -7 of 2-chloro-9-methoxy-1,6-diazaphenalene 2 and to convert 2, 17, 19 and 25 to the target compounds during the next year. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Dec 01, 1979
- Accession Number
- ADA111814
Entities
People
- James M Cook
Organizations
- University of Wisconsin Milwaukee Department of Chemistry and Biochemistry