A New Methodology for Functionalization at the 3-Position of Indoles by a Combination of Boron Lewis Acid with Nitriles

Kenta Mizoi, Yu Mashima, Yuya Kawashima, Masato Takahashi, Seisuke Mimori, Masakiyo Hosokawa, Yasuoki Murakami, Hiroshi Hamana
2015 Chemical and pharmaceutical bulletin  
We discovered that a reagent comprising a combination of PhBCl 2 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 NaBH 3 CN. These reactions proceeded
more » ... nder mild conditions and are applicable to the formation of indoles functionalized at the 3-position.
doi:10.1248/cpb.c15-00157 pmid:26133069 fatcat:32zxyqwiajffxleehysf7rrvte