Multicomponent Cyclizations of Ethyl Trifluoroacetoacetate with Acetaldehyde and 1,3-Diamines to Heteroannulated Pyridines
- Autores: Kushch S.O.1, Goryaeva M.V.1, Surnina E.A.1, Burgart Y.V.1, Saloutin V.I.1
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Afiliações:
- Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
- Edição: Volume 60, Nº 1 (2024)
- Páginas: 120-131
- Seção: Articles
- URL: https://ruspoj.com/0514-7492/article/view/672254
- DOI: https://doi.org/10.31857/S0514749224010118
- EDN: https://elibrary.ru/EMQGGT
- ID: 672254
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Resumo
A four-component approach was developed for the synthesis of cis- and trans-diastereomeric partially hydrogenated pyrido[1,2-a]pyrimidines and pyrido[2,1-b]quinazolines based on the cyclization of ethyl trifluoroacetoacetate with two acetaldehyde molecules and 1,3-diaminopropane or 2-aminomethylaniline. The zwitterionic salt of tetrahydropyrimidine was isolated as a by-product from the reaction with 1,3-diaminopropane. And from the reaction with 2-aminomethylaniline 7-hydroxy-7-(trifluoromethyl)-5,5a,6,7,8,11-hexahydro-9H-pyrido[2,1-b]quinazolin-9-one was obtained as a result of the participation of one aldehyde molecule. The diastereomeric structure of the synthesized heterocycles was established on the basis of 1Н, 19F, 13С NMR spectroscopy and XRD. A mechanism for the formation of new heteroannulated pyridines was proposed.
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Sobre autores
S. Kushch
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Autor responsável pela correspondência
Email: pmv@ios.uran.ru
ORCID ID: 0000-0002-7518-8998
Rússia, Ekaterinburg
M. Goryaeva
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: marinavgoryaeva@gmail.com
ORCID ID: 0000-0002-7853-688X
Rússia, Ekaterinburg
E. Surnina
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: pmv@ios.uran.ru
ORCID ID: 0000-0003-2961-6450
Rússia, Ekaterinburg
Ya. Burgart
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: pmv@ios.uran.ru
ORCID ID: 0000-0001-6061-2410
Rússia, Ekaterinburg
V. Saloutin
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: pmv@ios.uran.ru
ORCID ID: 0000-0003-1976-7861
Rússia, Ekaterinburg
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