1219010-36-2Relevant academic research and scientific papers
A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light
Hu, Qiang,Yu, Wan-Lei,Luo, Yong-Chun,Hu, Xiu-Qin,Xu, Peng-Fei
, p. 1493 - 1501 (2022/02/07)
Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi
Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes
Zheng, Jing,Deng, Ziyang,Zhang, Yan,Cui, Sunliang
, p. 746 - 751 (2016/03/09)
Most of the precedent copper-catalyzed trifluoromethylation reactions of unactivated alkenes concern terminal alkenes, and these processes are terminated in elimination, or nucleophilic addition, or semipinacol rearrangement, or C-H bond functionalization steps. In this study, we develop a trifluoromethylation method for both unactivated terminal and internal alkenes to enable divergent late-stage radical cyclization and achieve high molecular complexity. These cyclizations are well consistent with Baldwin's rule. Furthermore, a kinetic isotope effect (KIE) study and control reactions were conducted, and a plausible mechanism is proposed.
Radical migration of substituents of aryl groups on quinazolinones derived from N-Acyl cyanamides
Larraufie, Marie-Helene,Courillon, Christine,Ollivier, Cyril,Lacote, Emmanuel,Malacria, Max,Fensterbank, Louis
supporting information; experimental part, p. 4381 - 4387 (2010/05/15)
A newly designed radical cascade involving N-acyl cyanamides is reported. It builds on aromatic homolytic substitutions as intermediate events and leads to complex heteroaromatic structures via an unprecedented radical migration of a substituent on aryl groups of quinazolinones (hydrogen or alkyl). Mechanistic considerations are detailed, which allowed us to devise fine control over the domino processes. The latter could be predictably stopped at several stages, depending on the reaction conditions. Finally, a surgical introduction of a trifluoromethyl substituent on a quinazolinone was achieved via the reported migration.
