Autocatalytic photoinduced oxidative dehydrogenation of pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis of C5-C6 unsaturated systems with concomitant formation of a long-lived radical

Claudi de Rocafiguera, Vega Lloveras, José Vidal-Gancedo, Jordi Teixidó, Roger Estrada-Tejedor, José I. Borrell, Raimon Puig de la Bellacasa

Producción científica: Artículo en revista indizadaArtículorevisión exhaustiva

Resumen

5,6-Dihydropyrido[2,3-d]pyrimidin-7(8H)-ones are readily accessed by a variety of methods and are a good scaffold for the development of biologically active compounds. However, they are very reluctant to dehydrogenate to give C5-C6 unsaturated compounds, usually with higher activity. A serendipitous discovery has allowed us to develop an autocatalytic photochemical dehydrogenation process by irradiating at 450 or 365 nm in DMSO, in the presence of air, and at room temperature the corresponding 5,6-dihydro derivative (with a variety of substituents at C2, C4, C5, C6, and N8) without adding any external photosensitizer. A complete study including reactions in DMSO-d6 followed by NMR spectroscopy, EPR experiments, the use of radical quenchers, spin-trapping techniques, and reaction with methyl viologen, complemented with ab initio calculations has allowed us to propose a mechanistic rationalization for such a process.

Idioma originalInglés
Páginas (desde-hasta)27-36
Número de páginas10
PublicaciónOrganic Chemistry Frontiers
Volumen11
N.º1
DOI
EstadoPublicada - 2 nov 2023

Huella

Profundice en los temas de investigación de 'Autocatalytic photoinduced oxidative dehydrogenation of pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis of C5-C6 unsaturated systems with concomitant formation of a long-lived radical'. En conjunto forman una huella única.

Citar esto