A synthesis of 6-functionalized 4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines |
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Authors: | Maksim A Kolosov Elena H Shvets Dmitriy A Manuenkov Sergey A Vlasenko Irina V Omelchenko Svetlana V Shishkina Valeriy D Orlov |
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Institution: | 1. Department of Organic Chemistry, V.N. Karazin Kharkiv National University, Svobody sq., 4, 61022 Kharkiv, Ukraine;2. SSI “Institut for Single Crystals” NAS of Ukraine, Nauki ave, 60, 61001 Kharkiv, Ukraine |
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Abstract: | 6-Unsubstituted 7-R-4,7-dihydro-1,2,4-triazolo1,5-a]pyrimidines (R = H or Me) were synthesized via two pathways: (a) deacylation of the corresponding 5-acetyl Biginelli-like precursors in KOH/H2O and (b) reduction of the corresponding 1,2,4-triazolo1,5-a]pyrimidines using LiAlH4. The products could be easily formylated at position 6, which is promising for the further synthesis of functionalized 6-substituted derivatives of 4,7-dihydro-1,2,4-triazolo1,5-a]pyrimidines. In contrast, 6-acetyl-7-(4-(N,N-dimethylaminophenyl))-5-methyl-4,7-dihydro-1,2,4-triazolo1,5-a]pyrimidine undergoes a cascade process in KOH/H2O, leading to the formation of a 4,5,8,9-tetrahydro1,2,4]triazolo5,1-b]quinazoline derivative. |
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Keywords: | Biginelli-like reaction Deacylation |
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