An Easy and Efficient Synthesis of Bisindolylmethanes and Tetraindolylmethane Tröger's Base Catatlyzed by AgBF₄

Abstract

This work presents a highly efficient and simple method for the synthesis of bisindolylmethanes, catalyzed by AgBF 4 , with excellent yields. Various substituted aldehydes and ketones with indole under this reaction condition is elucidated. This reaction occurs efficiently under mild reaction conditions, such as are applied with methoxy or furfural, which commonly undergoes cleavage under strongly acidic reaction conditions. The presented approach was suitable for the synthesis of complex systems, such as tetraindolylmethane Tröger's Base.

Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or ModificationsviaSilver Tetrafluoroborate Mediation

“…In 1977, the first isolation of hallucinogenic bisindolylalkane was obtained and, subsequently, several bioactive bisindolylalkanes have been isolated from nature and this pulled a lot of scientific attention. Typically, some indole derivatives (3 substituted indoles) are known to exhibit various biological activities including antibacterial, cytotoxic, antioxidative, and insecticidal activities [88]. Following this line of thought, synthetic chemists in their pursuit for more efficient routes to synthesize the richly endowed indole molecules shifted from the common methods of preparing indole scaffold (Fischer, Bischler, Reissert, Madelung, and Smith methodologies) to organometallic reagents of which coinage metals (silver and gold) were the first choice [86].…”

Indole-3-acetamides: As Potential Antihyperglycemic and Antioxidant Agents; Synthesis, In Vitro α-Amylase Inhibitory Activity, Structure–Activity Relationship, and In Silico Studies

“… 23 , 24 Indomethacin and strychnine are among the most common biologically active synthetic and natural product resources that are derived from indole. 25 Indole and its related compounds possess a wide range of biological activities and are part of many medicinally important nuclei, which were widely accepted as pharmacophores. 26 Currently, indole nucleus has been found to be a part of more than 200 compounds that are marked as drugs or are undergoing clinical trials.…”

Green synthesis of AgI nanoparticle-functionalized reduced graphene oxide aerogels with enhanced catalytic performance and facile recycling

“…Dehydration resulted in the formation of the intermediate, which was activated again by the Ag + ions, and finally, the participation of a second mole of indole resulted in the final product, i.e., bis(indolyl)methane. 43 In addition to its catalytic activity, the reusability of a photocatalyst is important for practical applications. The reusability of the AgI-RGAs nanocomposite was successfully examined four times; we noticed a very slight loss of catalytic activity, which suggests that the present catalysts have good stability and sustainability.…”