Catalyst-free visible-light mediated a-alkylation of quinazolines and pyrrolo[2,1-f][1,2,4]triazine.
SANTOS, Jhonathan Renner Nunes dos; SCIOTA, Victor Biagio Argenton; VARGAS, Geovana Fontes; PINTO, Camila Batista; Giovanni Wilson Amarante; ELLENA, Javier; CORRÊA, Arlene Gonçalves.
SANTOS, Jhonathan Renner Nunes dos; SCIOTA, Victor Biagio Argenton; VARGAS, Geovana Fontes; PINTO, Camila Batista; Giovanni Wilson Amarante; ELLENA, Javier; CORRÊA, Arlene Gonçalves.
Abstract: Quinazolines are found in numerous commercially available drugs. Herein, we report a catalyst-free photochemical approach for the direct alkylation of these N-heterocycles under mild conditions. Additionally, late-stage functionalization of bioactive natural products-including caffeine, quinine derivative and flavone-was successfully achieved. Notably, the protocol also enabled the selective C7-functionalization of the pyrrolo[2,1-f][1,2,4]triazine core without requiring pre-functionalization, representing the first example of this transformation accomplished through a photochemical process. Using the optimized reaction condition, 17 alkylated heterocycles were prepared in 10-81% yield.
@article={003293393,author = {SANTOS, Jhonathan Renner Nunes dos; SCIOTA, Victor Biagio Argenton; VARGAS, Geovana Fontes; PINTO, Camila Batista; Giovanni Wilson Amarante; ELLENA, Javier; CORRÊA, Arlene Gonçalves.},title={Catalyst-free visible-light mediated a-alkylation of quinazolines and pyrrolo[2,1-f][1,2,4]triazine},journal={Tetrahedron},note={v. 195, p. 135195-1-135195-8 + supplementary data},year={2026}}