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Formylation of 4,7-Dihydro-1,2,4-triazolo[1,5-a]pyrimidines Using Vilsmeier-Haack Conditions

  作者 LIPSON VICTORIA V; SVETLICHNAYA NATALIYA V; BORODINA VICTORIA V; SHIROBOKOVA MARIA G; DESENKO SERGEY M; MUSATOV VLADIMIR I; SHISHKINA SVETLANA V; SHISHKIN OLEG V; ZUBATYUK ROMAN I  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2012年49-5;  页码  1019-1025  
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[摘要]Formylation of 5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine 1a using Vilsmeier-Haack conditions yields 5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a] pyrimidin-6-ylcarbaldehyde 3a. 5,7-Diaryl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines 1b,c in this reaction apart from formylation undergo recyclization into 5-aryl-1,2,4-triazolo[1,5-a]pyrimidin-6-ylmethane derivatives 4b,c, 5b,c, and 6. The structure of the synthesized compounds was determined on the basis of NMR, IR, and MS spectroscopic data and confirmed by the X-ray analysis of the 6-(ethoxy-phenyl-methyl)-5-phenyl[1,2,4]triazolo[1,5-a]pyrimidine 6, 5-phenyl-6-(1-phenyl-vinyl)-[1,2,4] triazolo[1,5-a]pyrimidine 11, and 7-phenyl-6-(1-phenyl-vinyl)-[1,2,4]triazolo[4,3-a]pyrimidine 12.

 
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