Synthesis and structural analysis of 5-cyanodihydropyrazolo[3,4-b]pyridines

被引：72
|
作者：
Quiroga, J [1 ]
Cruz, S
Insuasty, B
Abonia, R
Cobo, J
Sánchez, A
Nogueras, M
Low, JN
机构：
[1] Univ Valle, Dept Quim, Grp Invest Compuestos Heterociclicos, Cali AA25360, Colombia
[2] Univ Jaen, Dept Quim Inorgan & Organ, Jaen 23071, Spain
[3] Univ Dundee, Dept Appl Phys & Elect & Mfg Engn, Dundee DD1 4HN, Scotland
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2001年 / 38卷 / 01期
关键词：
D O I：
10.1002/jhet.5570380108
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several new 3-aryl-5-cyanopyrazolo[3,4-b]pyridines were easily prepared from 3-amino-5-arylpyrazoles and alpha -cyanochalcones. Structural analysis using NMR solution studies revealed the 2H-tautomers as the preferred tautomer in solution (DMSO-d(6)). X-ray diffraction confirmed the 2H-tautomers as the unique tautomer species in the crystalline state as well. Geometry optimization of 1H and 2H-tautomers at semi-empirical levels (AM1, MINDO/3) were performed, indicating that in all cases the 2H-tautomers are more stable than the corresponding 1H-tautomers.
引用
收藏
页码：53 / 60
页数：8
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