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

Autor: Pedro N. Batalha, Luana da S. M. Forezi, Maria Clara R. Freitas, Nathalia M. de C. Tolentino, Ednilsom Orestes, José Walkimar de M. Carneiro, Fernanda da C. S. Boechat, Maria Cecília B. V. de Souza
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 388-400 (2019)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.35
Popis: 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.
Databáze: Directory of Open Access Journals