title: A new methodology for functionalization at the 3-position of indoles by a combination of boron Lewis acid with nitriles.
abstract: We discovered that a reagent comprising a combination of PhBCl2 and nitriles was useful for syntheses of both 3-acylindoles and 1-(1H-indol-3-yl)alkylamine from indoles. The reaction proceeded selectively at the 3-position of indoles providing 3-acylindoles in moderate to high yields on treatment with the above reagent. Furthermore, the reaction provided the corresponding amine products in moderate to high yields after the intermediate imine was reduced by NaBH3CN. These reactions proceeded under mild conditions and are applicable to the formation of indoles functionalized at the 3-position.
authors.affiliation: Faculty of Pharmacy, Chiba Institute of Science.
authors.forename: Kenta
authors.initials: K
authors.lastname: Mizoi
authors.forename: Yu
authors.initials: Y
authors.lastname: Mashima
authors.forename: Yuya
authors.initials: Y
authors.lastname: Kawashima
authors.forename: Masato
authors.initials: M
authors.lastname: Takahashi
authors.forename: Seisuke
authors.initials: S
authors.lastname: Mimori
authors.forename: Masakiyo
authors.initials: M
authors.lastname: Hosokawa
authors.forename: Yasuoki
authors.initials: Y
authors.lastname: Murakami
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Hamana
mesh_terms: D000215:Acylation; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*
chemical_list: D000588:Amines; D001894:Borohydrides; D007097:Imines; D007211:Indoles; D058116:Lewis Acids; D009570:Nitriles; C009282:sodium cyanoborohydride