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Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide.

ABSTRACT: 4-Oxoquinolines are a class of organic substances of great importance in medicinal chemistry, due to their biological and synthetic versatility. N-1-Alkylated-4-oxoquinoline derivatives have been associated with different pharmacological activities such as antibacterial and antiviral. The presence of a carboxamide unit connected to carbon C-3 of the 4-oxoquinoline core has been associated with various biological activities. Experimentally, the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide occurs at the nitrogen of the oxoquinoline group, in a regiosselective way. In this work, we employed DFT methods to investigate the regiosselective ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide, evaluating its acid/base behavior and possible reaction paths.

SUBMITTER: Batalha PN 

PROVIDER: S-EPMC6404479 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Study on the regioselectivity of the N-ethylation reaction of <i>N</i>-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide.

Batalha Pedro N PN   Forezi Luana da S M LDSM   Freitas Maria Clara R MCR   Tolentino Nathalia M de C NMC   Orestes Ednilsom E   Carneiro José Walkimar de M JWM   Boechat Fernanda da C S FDCS   de Souza Maria Cecília B V MCBV  

Beilstein journal of organic chemistry 20190212

4-Oxoquinolines are a class of organic substances of great importance in medicinal chemistry, due to their biological and synthetic versatility. <i>N</i>-1-Alkylated-4-oxoquinoline derivatives have been associated with different pharmacological activities such as antibacterial and antiviral. The presence of a carboxamide unit connected to carbon C-3 of the 4-oxoquinoline core has been associated with various biological activities. Experimentally, the N-ethylation reaction of <i>N</i>-benzyl-4-ox  ...[more]

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