18212-32-3Relevant articles and documents
Metal-free C8-H functionalization of quinolineN-oxides with ynamides
Hu, Weican,Zhang, Feiyang,Chen, Chen,Qi, Tianhang,Shen, Yanlong,Qian, Guoying,Rong, Zhouting
supporting information, p. 6995 - 6998 (2021/07/21)
The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox
Synthesis of Isothiochroman-3-ones via Metal-Free Oxidative Cyclization of Alkynyl Thioethers
Zhang, Ying-Qi,Zhu, Xin-Qi,Chen, Yang-Bo,Tan, Tong-De,Yang, Ming-Yang,Ye, Long-Wu
supporting information, p. 7721 - 7725 (2019/01/03)
A novel Br?nsted acid-catalyzed oxidative C-H functionalization of alkynyl thioethers has been developed. This method allows the practical synthesis of valuable isothiochroman-3-ones in mostly moderate to good yields under mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, this metal-free oxidation can also be used to promote formal N-H insertion involving an unexpected 1,2-sulfur migration, affording useful 1,4-benzothiazin-3-ones.
Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
Racine, Sophie,Hegedüs, Bence,Scopelliti, Rosario,Waser, Jér?me
supporting information, p. 11997 - 12001 (2016/08/16)
Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.