N. Colbry, E. Elslager, L. M. Werbel
Sep 1, 1984
Citations
0
Influential Citations
18
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The synthesis and antimalarial activity of a series of 2,4-diamino-6-[(aryl)thio, sulfinyl and sulfonyl]pyrido-[3,2-d]pyrimidines is described. Nitration of 2,6-dichloropyridine provided the 3-nitro derivative which was converted to 6-chloro-3-nitro-2-pyridinecarbonitrile (V) with cuprous cyanide. Condensation of an aryl thiol with V gave the 6-arylthiopyridines VI which were reduced with iron in hydrochloric acid and condensed with chloroformamidine to give the 6-arylthiopyrido[3,2-d]pyrimidin-2,4-diamines X. Alternatively V was reduced to the amine VIII condensed with chloroformamidine and the resulting 6-chloropyrido[3,2-d]pyrimidine (IX) was treated with an arylthiol. Oxidation of X provided sulfinyl and sulfonyl analogs.