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A synthesis of 6-functionalized 4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2017-02-25 07:24:25
Maksim A. Kolosov, Elena H. Shvets, Dmitriy A. Manuenkov, Sergey A. Vlasenko, Irina V. Omelchenko, Svetlana V. Shishkina, Valeriy D. Orlov

6-Unsubstituted 7-R-4,7-dihydro-1,2,4-triazolo[1,5-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-triazolo[1,5-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-triazolo[1,5-a]pyrimidines. In contrast, 6-acetyl-7-(4-(N,N-dimethylaminophenyl))-5-methyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine undergoes a cascade process in KOH/H2O, leading to the formation of a 4,5,8,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazoline derivative.

中文翻译:

6-官能化的4,7-二氢[1,2,4]三唑并[1,5-a]嘧啶的合成

通过两种途径合成6-未取代的7-R-4,7-二氢-1,2,4-三唑并[1,5-a]嘧啶(R = H或Me):(a)相应的5-脱酰基KOH / H 2 O中的乙酰基Biginelli状前体,以及(b)使用LiAlH 4还原相应的1,2,4-三唑并[1,5-a]嘧啶。产物可以容易地在位置6处被甲酰化,这对于进一步合成4,7-二氢-1,2,4-三唑并[1,5-a]嘧啶的官能化的6-取代的衍生物是有希望的。相反,6-乙酰基-7-(4-(N,N-二甲基氨基苯基))-5-甲基-4,7-二氢-1,2,4-三唑并[1,5-a]嘧啶经历了级联过程在KOH / H 2 O中,导致形成4,5,8,9-四氢[1,2,4]三唑并[5,1-b]喹唑啉衍生物。
更新日期:2017-02-25
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