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Paper | Special issue | Vol 93, No. 2, 2016, pp.705-713
Published online, 6th January, 2016
DOI: 10.3987/COM-15-S(T)60
Facile Synthesis of 5- to 7-Membered Benzolactam Compounds via Strongly Facilitated Electrophilic Aromtic Substitution Reaction

Hiroaki Kurouchi, Yuko Otani, and Tomohiko Ohwada*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

We employed our system to activate aromatic ring-tethered carbamate compounds with trifluoromethanesulfonic acid to obtain benzolactams with 5- to 7-membered rings, and examined the substrate scope and limitations of this activation method. In 5-membered ring formation, a halogen group on the aromatic ring did not greatly affect the reaction yield, but other electron-donating groups inhibited the cyclization reaction, and various side-reactions occurred. In 7-membered ring formation, eletron-donating groups on aromatic ring promoted the cyclization reaction, but cyclization of electron-deficient aromatic rings did not proceed well. The 6-membered ring formation reaction showed the greatest substrate generality.