4-Hydroxy-2-quinolones 150*. Efficient synthesis, structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides

Украинец, И. В.; Bereznyakova, N. L.; Паршиков, В. А.; Gorokhova, O. V.

doi:10.1007/s10593-009-0209-7

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“…We have previously proposed the preparation of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamides and this has been introduced satisfactorily into the synthesis of N-alkyl- [2], arylalkyl- [3], and aryl- [4] substituted derivatives. There are differences in some details of carrying out the experiment but a common feature is shared, i.e.…”

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4-hydroxy-2-quinolones. 153*. Synthesis of hetarylamides of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Украинец

Bereznyakova

Паршиков

2009

Chem Heterocycl Comp

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Keywords: 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid, amidation, intramolecular cyclization.We have previously proposed the preparation of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamides and this has been introduced satisfactorily into the synthesis of N-alkyl-[2], arylalkyl- [3], and aryl-[4] substituted derivatives. There are differences in some details of carrying out the experiment but a common feature is shared, i.e. all are based on the initial separation of the corresponding quinoline-3-carboxylic acid. In most cases such a course was justified even though the method of activating the carbonyl carbon atom of the carboxyl group in the starting quinoline-3-carboxylic acid has to be modified each time based on the properties of the starting amine.One of the reported methods can evidently also be used for synthesis of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hetarylamides 1. It should immediately be noted, however, that when 2-oxo-1,2-dihydroquinoline-3-carboxylic acid chlorides react with azahetarylamines they frequently form stable N-acylhetarylamine salts rather than the amides [5]. For this reason we have not studied the "acid chloride" variant in this work. The use here of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid imidazolide (2) as the acylating agent appears more promising and, in fact, shows fully satisfactory results (method A, Table 1). None the less it has been noted before [4] that the imidazolide 2 is unusually unreactive and thus needs the use of high boiling solvents and in some cases has led to serious complications. Hence, for example, with acylation of the thermally unstable 2-amino-5-isobutyl-1,3,4-thiadiazole under these conditions the corresponding hetarylamide 1n could be obtained, but due to the low reaction rate it proved to be so strongly charged with gray-brown colored degradation products of the free amine that purification of the final product proved impossible even

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4-hydroxy-2-quinolones. 153*. Synthesis of hetarylamides of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Украинец

Bereznyakova

Паршиков

2009

Chem Heterocycl Comp

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ChemInform Abstract: 4‐Hydroxy‐2‐quinolones. Part 150. Efficient Synthesis, Structure, and Biological Activities of 4‐Methyl‐2‐oxo‐1,2‐dihydroquinoline‐3‐carboxylic Acid Alkyl Amides.

et al. 2009

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15.4.5 Quinolinones and Related Systems (Update 2022)

Silva¹,

Pinto²,

Santos³

et al. 2022

Knowledge Updates 2022/3

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Quinolinones, of which the quinolin-4(1H)-one ring system can be highlighted, represent an exciting class of nitrogen heterocycles. The quinolinone motif can be found in many natural compounds and approved drugs for several diseases. This chapter is a comprehensive survey of the methods for the synthesis of quinolin-2(1H)-ones, quinolin-4(1H)-ones, and their thio- and amino derivatives, and is an update to the previous Science of Synthesis chapter (Section 15.4), covering the period between 2003 and 2020.

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4-Hydroxy-2-quinolones 150*. Efficient synthesis, structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides

Abstract: A simple and efficient method for preparing 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides is proposed. The results of a study of the diuretic activity of the compounds synthesized are reported.

Cited by 4 publications

References 4 publications

4-hydroxy-2-quinolones. 153*. Synthesis of hetarylamides of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

4-hydroxy-2-quinolones. 153*. Synthesis of hetarylamides of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

ChemInform Abstract: 4‐Hydroxy‐2‐quinolones. Part 150. Efficient Synthesis, Structure, and Biological Activities of 4‐Methyl‐2‐oxo‐1,2‐dihydroquinoline‐3‐carboxylic Acid Alkyl Amides.

15.4.5 Quinolinones and Related Systems (Update 2022)

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