The FeCl3·6H2O-catalyzed three-component aza-Friedel-Crafts reaction of aromatic/heteroaromatic compounds, aromatic aldehydes and tert-butyl carbamate was reported. The subsequent Friedel-Crafts-type alkylation of the resulting tert-butyl diarylmethyl carbamate with heteroaromatic compounds under "open-flask" at room temperature was also performed. The two-step reaction was especially useful for the synthesis of functionalized nonsymmetrical heteroaryl-substituted triarylmethanes in good yields under an air atmosphere at room temperature.
Brönsted acidic ionic liquid catalyzed the synthesis of aniline- and phenol-based triarylmethanes via Friedel-Crafts reaction under metal- and solvent-free conditions.
A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature. Notably, SO3H-ILs, 1-butylsulfonic-3-methylimidazolium hydrogen sulfate ([bsmim][HSO4]) was the most efficient catalyst for moderate to good yields of the corresponding desired products.
A first and short total synthesis
of the marine sponge 2,3′-bis(indolyl)ethylamine
(2,3′-BIEA) alkaloid (±)-gelliusine E was performed in
both a three-step divergent approach and a one-pot three-component
approach with an overall yield of up to 58%. A key feature of the
novel strategy is PTSA-catalyzed transindolylation of the readily
synthesized 3,3′-BIEAs with tryptamine derivatives. The structure
of the isolated natural product is revised as protonated (±)-gelliusine
E (4′). By design, this modular route allows the rapid synthesis
of other members of the 2,3′-BIEA family, for example, (±)-6,6′-bis-(debromo)-gelliusine
F and analogues with step economy, operational simplicity, and reduced
waste. Furthermore, their cytotoxicity in breast cancer cells was
investigated.
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