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

Autor:	A. V. Bol’but, M. V. Vovk, Georgiy G. Yakovenko, Oleh А. Lukianov
Rok vydání:	2019
Předmět:	010405 organic chemistry Chemistry Organic Chemistry Malonic acid 010402 general chemistry 01 natural sciences Medicinal chemistry Pyrrolidine 0104 chemical sciences Catalysis chemistry.chemical_compound Cyanoacetic acid Pyridine Proline Monomethyl ether
Zdroj:	Chemistry of Heterocyclic Compounds. 55:1211-1216
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-019-02603-5
Popis:	N-Boc-protected 5-formyl-1H-pyrazol-4-amines react with malonic acid in pyridine in the presence of pyrrolidine at 45–50°С 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°С 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.
Databáze:	OpenAIRE
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