New Efficient Synthesis of 5,6-Disubstituted-3-phenyl-1,2,3-triazolo[4,5-d]pyrimidin-7-ones via a Tandem Aza-Wittig Reaction

Abstract

Twelve novel 5,6-disubstituted-3-phenyl-1,2,3-triazolo[4,5-d]pyrimidine-7-ones 5a–5l were designed and successfully synthesized via tandem aza-Wittig and annulation reactions of the corresponding iminophosphorances 2, aromatic isocyanate, and substituted thiophenols in satisfactory yields. The results from the preliminary bioassay indicated that some of these compounds possess inhibitory activities against the root and stalk of Brassica napus(rape) as well as Echinochloa crusgalli (barnyard grass) at the dosages of 100 mg/L and 10 mg/L, respectively.

GRAPHICAL ABSTRACT

Keywords:

• Aza-Wittig reaction
• herbicidal activity
• synthesis
• 1,2,3-triazolo[4,5-d]pyrimidine-7-ones

ACKNOWLEDGMENTS

We thank the National Natural Science Foundation of China (No. 20862007) and the Natural Science Foundation of Jiangxi Province in China (No. 2007GZH1399) for financial support.