Al(OTf)₃‐Catalyzed Tandem Coupling Reaction between N,N‐Disubstituted Aminomalonitriles and Substituted Arenes: a Synthesis of 1‐Cyano‐bisindolylmethane Analogues^≠

Abstract

A synthesis of 1‐cyano‐bisindolylmethane analogues via an Al(OTf)3‐catalyzed tandem coupling reaction between N,N‐disubstituted aminomalonitriles and substituted arenes has been developed. This method not only provides an alternative synthetic strategy for the synthesis of corresponding functional molecules, but also enriches the volume of bisarylmethanes library to facilitate related functional studies.magnified image

Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives

“…As an important class of indole alkaloids, bis(indolyl)methanes (BIM) broadly exist in many bioactive natural products [1][2][3][4][5], such as streptindole [6], arsindoline A [7], trisindoline [8], and a wide range of biological activities, such as antibacterial, antitumor and antileishmanial properties, were shown in these related compounds (Scheme 1a). Therefore, the synthesis of a bis(indolyl)methane (BIM) type of structure has attracted broad attention in synthetic chemistry [1,[9][10][11][12][13][14][15][16]. Generally, 3-alkyl-bis(indolyl)methanes were obtained easily via a Lewis or Brønsted acid-catalyzed double Friedel-Crafts reaction between indole and carbonyl compounds (Scheme 1b).…”

In vitro and in silico studies of bis (indol-3-yl) methane derivatives as potential α-glucosidase and α-amylase inhibitors

“…Based on the principle of combination of active structural moieties in drug design and our synthetic methodology for BIMs derivatives, 29 we synthesised BIMs derivatives to evaluate them for their α-glucosidase and α-amylase inhibitory activity.…”