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Short Paper | Regular issue | Vol 96, No. 5, 2018, pp.910-920
Published online, 12th April, 2018
DOI: 10.3987/COM-18-13888
Synthesis of 3-Aroylindoles as Intermediates of Cannabimimetics and Elucidation of Their Physicochemical Properties

Koji Araki, Kosho Makino, Hidetsugu Tabata, Hiroshi Nakayama, Kei Zaitsu, Tetsuta Oshitari, Hideaki Natsugari, and Hideyo Takahashi*

*Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo, 173-8605, Japan


In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the 1H NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.