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Note | Regular issue | Vol 68, No. 11, 2006, pp.2387-2402
Published online, 12th September, 2006
DOI: 10.3987/COM-06-10869
■ Synthesis and Antiviral and Antitumor Activities of 2H-[1,2,3]Triazolo[4,5-d]pyrimidines and 1H-, 2H-, and 3H-[1,2,3]Triazolo[4,5-d]pyrimidin-5(4H)-one-7(6H)-thiones

Rafiqul Islam and Tomohisa Nagamatsu*

*Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700-8530, Japan

Abstract

This paper describes a facile synthesis of 2-aryl-2H-[1,2,3]triazolo- [4,5-d]pyrimidine-5,7(4H,6H)-diones (3a-o) and 7-amino-2-aryl-5-phenyl-2H- [1,2,3]triazolo[4,5-d]pyrimidines (6a-e) prepared by oxidative cyclization of 6- amino-5-arylazopyrimidine-2,4(1H,3H)-diones (2a-o) and 4,6-diamino-5- arylazo-2-phenylpyrimidines (5a-e) with CuSO4, respectively, and a reliable thionation of [1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (3a,e,f, 7a,b and 9) accomplished by the reaction with phosphorous pentasulfide or Lawesson’s reagent as well as evaluation of their antiviral and antitumor activities in vitro.