Accession Number : ADA111814

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

Descriptive Note : Annual summary rept. 1 Jan-31 Dec 79,


Personal Author(s) : Cook,James M

PDF Url : ADA111814

Report Date : Dec 1979

Pagination or Media Count : 30

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)

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

Subject Categories : Pharmacology

Distribution Statement : APPROVED FOR PUBLIC RELEASE