98262-85-2Relevant academic research and scientific papers
Visible-Light Photoredox Catalyzed Oxidative/Reductive Cyclization Reaction of N-Cyanamide Alkenes for the Synthesis of Sulfonated Quinazolinones
Qian, Ping,Deng, Yu,Mei, Haibo,Han, Jianlin,Zhou, Jie,Pan, Yi
supporting information, p. 4798 - 4801 (2017/09/23)
An efficient photocatalytic oxidative/reductive cyclization reaction of N-cyanamide alkenes with arylsulfinic acids or arylsulfonyl chlorides, which proceeds through C-S, C-C, and C-N bond formations, is reported. This photocatalytic reaction was carried out under mild conditions, which provides a new strategy for the synthesis of sulfonated quinazolinones. Furthermore, a one-pot procedure to achieve terminal alkenes has been explored via elimination of the obtained sulfonated quinazolinones under basic conditions.
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.
