Browsing by Author "Ye, Tzuen-Yang"

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Cascade Synthesis of Benzimidazole-Linked Pyrroles via Copper Catalyzed Oxidative Cyclization and Ketonization
(2017-06-16)
Ye, Tzuen-Yang
;
Selvaraju, Manikandan
;
Sun, Chung-Ming
;
應用化學系
;
Department of Applied Chemistry
A three-component cascade reaction of 2-aminobenzimidazole, aldehyde, and terminal alkyne has been explored for an efficient synthesis, of benzimidazole-linked tetrasubstituted pyrroles. The reaction sequence involves the formation Of propargylamine, insertion of 4 terminal alkyne, and a ring opening reaction, followed by, an intramolecular carboylative cyclization under aerobic conditions. It represents a novel, strategy to the construction of C=N, C=C, C=0 bonds and a new five-membered 2-ketopyrrole ring. In this process, the reaction conditions are crucial and an attempt to elucidate the novel reaction patway is well, supported by X=ray crystallography.
Copper catalyzed aerobic oxidative cyclization and ketonization: one pot synthesis of benzoimidazo[1,2-a]imidazolones
(2016)
Selvaraju, Manikandan
;
Ye, Tzuen-Yang
;
Li, Chia-Hsin
;
Ho, Pei-Heng
;
Sun, Chung-Ming
A highly efficient synthesis of benzoimidazo[1,2-a]imidazolone through a novel oxidative 5-exo-dig cyclization-ketonization cascade of 2-aminobenzimidazole, aldehyde and terminal alkyne has been explored under aerobic conditions. The reaction proceeds through copper-catalyzed addition of terminal alkynes to imines derived from 2-aminobenzimidazole with aldehyde followed by intramolecular cyclization. The atmospheric molecular oxygen acts as an oxygen source for the newly formed carbonyl group in the final product.