6-(Pyrazol-1-yl)pyrazolo[3,4-b]pyridines: Synthesis, Structure, and Wheat Growth Regulating Activity

被引：0

作者：

Dmitrieva, I. G. ^{[1
]}

Vasilin, V. K. ^{[2
]}

Dotsenko, V. V. ^{[3
,4
]}

Aksenov, N. A. ^{[4
]}

机构：

[1] IT Trubilin Kuban State Agrarian Univ, Krasnodar 350044, Russia

[2] Kuban State Technol Univ, Krasnodar 350072, Russia

[3] Kuban State Univ, Krasnodar 350040, Russia

[4] North Caucasus Fed Univ, Stavropol 355009, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 10期

基金：

俄罗斯科学基金会;

关键词：

6-hydrazino-2-chloronicotinonitrile; Knorr synthesis; alkylhydrazines; dealkylation; 3-aminopyrazolo[3,4-b]pyridines; acylation; carbamoylation; wheat growth regulators; ONE-POT SYNTHESIS; HETEROCYCLIZATION REACTIONS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; DERIVATIVES; DISCOVERY; PYRAZOLES; KETONES; 5-AMINO-3-(CYANOMETHYL)-1H-PYRAZOLE-4-CARBONITRILE; CONVENIENT;

D O I：

10.1134/S1070363224100050

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

4-Methyl-6-pyrazolyl-2-chloronicotinonitriles were synthesized by the reaction of 6-hydrazino-4-methyl-2-chloronicotinonitriles with 1,3-diketones. Upon treatment with hydrazine and methylhydrazine, 4-methyl-6-pyrazolyl-2-chloronicotinonitriles were converted into the corresponding 3-amino-4-methyl-6-pyrazolyl-1H-pyrazolo[3,4-b]pyridines. A similar reaction involving 1,1-dimethylhydrazine and ethylhydrazine was accompanied by elimination of the alkyl substituent and also led to the formation of 3-amino-6-pyrazolyl-1H-pyrazolo[3,4-b]pyridines. Acylation and carbamoylation of the prepared compounds proceeded regioselectively at the amino group. One of the new compounds, N-[6-(3,5-dimethylpyrazol-1-yl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl]cyclopropanoylamide, showed a growth-stimulating effect in the field experiments on winter wheat crops.

引用

页码：2603 / 2615

页数：13

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