Synthesis of Fluorescent Pyrrolo[1,2-<i>a</i>]pyrimidines from Fischer Carbene Complexes as Building Blocks.

Velazco-Cabral, Iván; Vázquez, Juan Luis; Alcaraz-Contreras, Yolanda; Delgado, Francisco; Peña-Cabrera, Eduardo; García Revilla, Marco A; Vázquez, Miguel A

Synthesis of Fluorescent Pyrrolo[1,2-a]pyrimidines from Fischer Carbene Complexes as Building Blocks.

Velazco-Cabral, Iván; Vázquez, Juan Luis; Alcaraz-Contreras, Yolanda; Delgado, Francisco; Peña-Cabrera, Eduardo; García Revilla, Marco A; Vázquez, Miguel A.

Afiliação

Velazco-Cabral I; Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.
Vázquez JL; Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.
Alcaraz-Contreras Y; Departamento de Farmacia, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.
Delgado F; Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala S/N, 11340 Cd. de México, Mexico.
Peña-Cabrera E; Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.
García Revilla MA; Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.
Vázquez MA; Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto, Mexico.

J Org Chem ; 88(14): 9615-9628, 2023 Jul 21.

Article em En | MEDLINE | ID: mdl-37307088

RESUMO

A novel synthetic methodology is reported for the synthesis of fluorescent pyrrolo[1,2-a]pyrimidines. Fischer carbene complexes served as the synthetic platform for (3+3) cyclization to form the heterocyclic moiety. The reaction process furnished two products, their ratio being modulated by the metal, base, and solvent. The selectivity exhibited was studied by analyzing the potential energy surface with density functional theory tools. The photophysical properties of absorption and emission were also evaluated. The dyes absorbed at wavelengths of 240-440 nm, depending on the substituents. The maximum emission wavelength was in the range of 470-513 nm, with quantum yields of 0.36-1.0 and a high Stokes shift range of 75-226 nm.

Texto completo

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2023 Tipo de documento: Article País de afiliação: México País de publicação: Estados Unidos

Texto completo

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Buscar no Google