Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds

被引：11
|
作者：
Nikpassand, Mohammad [1 ]
Fekri, Leila Zare [2 ]
Rahro, Parissa Naddaf [1 ]
机构：
[1] Islamic Azad Univ, Rasht Branch, Dept Chem, Rasht, Iran
[2] Payame Noor Univ, Dept Chem, POB 19395-3697, Tehran, Iran
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2019年 / 45卷 / 04期
关键词：
Grinding reaction; DFT; Mechanism; Intermediate; Transition state; C-13; NMR-SPECTRA; ANTIMICROBIAL ACTIVITY; CRYSTAL-STRUCTURE; FT-IR; DERIVATIVES; NITROALKENES; REACTIVITY; INHIBITORS; DESIGN; POTENT;
D O I：
10.1007/s11164-018-3701-9
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel, efficient, one-pot, catalyst-free grinding procedure for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile is reported. The condensation of substitutedbenzaldehydes, 3-amino-5-methylpyrazole, and malononitrile according to a three-component reaction was investigated using density functional theory (DFT) at B3LYP/6-311G level to explore the reaction mechanism. All the routes were studied, the structure of the intermediates was optimized, and all the respective transition states were found. The results of the calculations show that the proposed mechanism relies on four intermediates.
引用
收藏
页码：1707 / 1719
页数：13
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