A convenient synthesis method of 5-oxopyrazolo[4,3-b]pyridine-6-carboxylic acids and their nitriles

被引：4
|
作者：
Yakovenko, Georgiy G. [1 ,2 ]
Lukianov, Oleh A. [2 ]
Bol'but, Andriy, V [2 ,3 ]
Vovk, Mikhailo V. [2 ]
机构：
[1] Natl Univ Kyiv Mohyla Acad, 2 Hrygorija Skorovody St, UA-04655 Kiev, Ukraine
[2] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska St, UA-02094 Kiev, Ukraine
[3] Enamine Ltd, 78 Chervonotkatskaya St, UA-02094 Kiev, Ukraine
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2019年 / 55卷 / 12期
关键词：
cyanoacetic acid; 5-formyl-1H-pyrazol-4-amine; malonic acid; methyl cyanoacetate; monomethyl malonate; pyrazolo[4,3-b]-pyridine-6-carbonitrile; pyrazolo[4,3-b]pyridine-6-carboxylic acid; cyclocondensation; POTENT;
D O I：
10.1007/s10593-019-02603-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Boc-protected 5-formyl-1H-pyrazol-4-amines react with malonic acid in pyridine in the presence of pyrrolidine at 45-50 degrees C or with malonic acid monomethyl ether in the presence of pyrrolidine in AcOH under reflux with the formation of 5-oxo-4,5-dihydro-1Hpyrazolo[4,3-b]pyridine-6-carboxylic acids. The reaction of N-Boc-protected 5-formyl-1H-pyrazol-4-amines with cyanoacetic acid in pyridine in the presence of pyrrolidine at 45-50 degrees C leads to the formation of 5-oxo-4,5-dihydro-1H-pyrazolo[4,3-b]pyridine-6-carbonitriles. The latter can also be obtained via cyclocondensation of N-Boc-protected 5-formyl-1H-pyrazol-4-amines with methyl cyanoacetate in AcOH under reflux in the presence of pyrrolidine or in MeCN containing pyrrolidine and a catalytic amount of proline heated under reflux.
引用
收藏
页码：1211 / 1216
页数：6
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