Formylation of 4,7‐Dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidines Using Vilsmeier–Haack Conditions |
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| Authors: | Victoria V Lipson Nataliya V Svetlichnaya Victoria V Borodina Maria G Shirobokova Sergey M Desenko Vladimir I Musatov Svetlana V Shishkina Oleg V Shishkin Roman I Zubatyuk |
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| Institution: | 1. Antidiabetic Drug Laboratory of Medicinal Chemistry Department, State Institution, “V.Ya. Danilevsky Institute for Endocrine Pathology Problems” of Academy of Medical Sciences of Ukraine, , Kharkov, 61002 Ukraine;2. Department of Chemistry, V.N. Karazin Kharkov National University, , Kharkov, 61077 Ukraine;3. Division of Functional Materials Chemistry, State Scientific Institution, “Institute for Single Crystals” of National Academy of Sciences of Ukraine, , Kharkov, 61001 Ukraine |
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| Abstract: | Formylation of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo1,5‐a]pyrimidine 1a using Vilsmeier–Haack conditions yields 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo1,5‐a]pyrimidin‐6‐ylcarbaldehyde 3a . 5,7‐Diaryl‐4,7‐dihydro‐1,2,4‐triazolo1,5‐a]pyrimidines 1b , 1c in this reaction apart from formylation undergo recyclization into 5‐aryl‐1,2,4‐triazolo1,5‐a]pyrimidin‐6‐ylmethane derivatives 4b , 4c , 5b , 5c , 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]triazolo1,5‐a]pyrimidine 6 , 5‐phenyl‐6‐(1‐phenyl‐vinyl)‐1,2,4]triazolo1,5‐a]pyrimidine 11 , and 7‐phenyl‐6‐(1‐phenyl‐vinyl)‐1,2,4]triazolo4,3‐a]pyrimidine 12 . |
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