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

页码：53 / 60

页数：8

共 50 条

[31] SYNTHESIS OF 3-ARYL-6H-ISOXAZOLO[3,4-D]PYRAZOLO[3,4-B]PYRIDINES AND 3-ARYL-6H-ISOXAZOLO[5,4-D]PYRAZOLO[3,4-B]PYRIDINES
SHUTSKE, GM
HUGER, FP
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) : 703 - 709
[32] REACTIONS OF 4-ARYLMETHYLENEPYRROLIDINE-2,3-DIONES - SYNTHESIS OF PYRROLO[3,4-B]-PYRIDINES AND PYRROLO[3,4-B]-QUINOLINES
MADHAV, R
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (18): : 2108 - 2110
[33] Convenient synthesis of functionalized pyrrolo[3,4-b]pyridines and pyrrolo[3,4-b]quinolines via three-component reactions
Jiang, Yan-Hong
Xiao, Man
Yan, Chao-Guo
RSC ADVANCES, 2016, 6 (42) : 35609 - 35616
[34] SYNTHESIS OF PYRIDO[3,4-B]PYRANO[3,4-B]INDOLES
FRETER, K
FUCHS, V
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) : 377 - 379
[35] Synthesis of novel dipyrazolo[3,4-b:3,4-d]pyridines and study of their fluorescence behavior
Kendre, Dhananjay B.
Toche, Raghunath B.
Jachak, Madhukar N.
TETRAHEDRON, 2007, 63 (45) : 11000 - 11004
[36] Synthesis of some new bipyridines, thieno[2,3-b]pyridines, and pyrazolo[3,4-b]pyridines
Mohamed, Mahmoud A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (01) : 200 - 203
[37] SYNTHESIS OF ISOTHIAZOLO[5,4-B]PYRIDINES
MAHALANABIS, KK
SARKAR, M
CHATTOPADHYAY, S
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (05): : 458 - 460
[38] ISOTHIAZOLOPYRIDINES .1. SYNTHESIS AND SPECTRA OF ISOTHIAZOLO[3,4-B]-PYRIDINES, 3-AMINOISOTHIAZOLO[4,3-B]-PYRIDINES, ISOTHIAZOLO[5,4-B]-PYRIDINES, AND "3-METHYLISOTHIAZOLO[5,4-C]PYRIDINES - PREPARATION AND SPECTRA OF SOME 2,3-DISUBSTITUTED AND 3,4-DISUBSTITUTED PYRIDINES
TAURINS, A
KHOUW, VT
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (11): : 1741 - 1748
[39] AZAINDOLES .3. SYNTHESIS OF PYRAZOLO[3,4-B]PYRIDINES AND PYRAZOLO[3,4-D]PYRIMIDINES
BADGER, GM
RAO, RP
AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (08) : 1267 - &
[40] Synthesis and nucleophilic dearomatization of highly electrophilic [1,2,5]selenadiazolo[3,4-b]pyridines
V. V. Ivanova
A. K. Fedorenko
A. M. Starosotnikov
M. A. Bastrakov
Russian Chemical Bulletin, 2022, 71 : 1826 - 1829

← 1 2 3 4 5 →