2015
DOI: 10.1248/cpb.c15-00157
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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 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 under mild condi… Show more

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Cited by 5 publications
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“…PhBCl 2 , it was exploited as catalyst of choice by Hamana et al, to afford C3 substituted indoles. 80 Interestingly, in this work the reaction partner was a nitrile that, upon reaction with indole, gave an iminium intermediate whose fate was decided by the reaction conditions. In fact, while hydrolysis generated 3acylindoles, reduction in the presence of NaBH 3 CN led to 1-(1Hindol-3-yl) alkylamines (Scheme 21b).…”
Section: Scheme 20 Bf 3 -Promoted Indole C3-aza Alkylationmentioning
confidence: 90%
“…PhBCl 2 , it was exploited as catalyst of choice by Hamana et al, to afford C3 substituted indoles. 80 Interestingly, in this work the reaction partner was a nitrile that, upon reaction with indole, gave an iminium intermediate whose fate was decided by the reaction conditions. In fact, while hydrolysis generated 3acylindoles, reduction in the presence of NaBH 3 CN led to 1-(1Hindol-3-yl) alkylamines (Scheme 21b).…”
Section: Scheme 20 Bf 3 -Promoted Indole C3-aza Alkylationmentioning
confidence: 90%