Nucleophilic Addition Of Indoles Research Articles

Triflic Acid-Catalyzed Synthesis of Indole-Substituted Indane Derivatives via In Situ Formed Acetal-Facilitated Nucleophilic Addition and 4π-Electron-5-Carbon Electrocyclization Sequence.

An efficient protocol for the synthesis of indole-substituted indanes from o-alkenylbenzaldehydes under acetalization conditions has been presented. The cyclization occurs via a nucleophilic addition of indole on the oxacarbenium ion generated from acetal formed under the reaction condition followed by a conrotatory 4π-electrocyclization reaction, which takes care of the exclusive diastereoselectivity observed during the cyclization step. Olefin geometry of o-alkenylbenzaldehyde and the amount of indole play a decisive role in the success of this cyclization process.

Synthesis of Potential Anticancer 1-(1H-Indol-3-yl)isoquinolines by Silver Nitrate Mediated Tandem Reactions of 2-Alkynyl­benzaldehyde Azines and Indoles

Novel antitumor compounds featuring isoquinoline and indole moieties were synthesized by a silver nitrate promoted domino reaction involving intramolecular cyclization, nucleophilic addition of indole, and subsequent N–N bond cleavage. The transformation from readily available starting materials into an interesting class of indole-substituted isoquinolines was completed under mild conditions and by simple operations in moderate to good yields. The antitumor activity of these compounds in vitro was significantly greater than that of a reference compound, 5-fluorouracil. The products might serve as new lead compounds for drugs for the treatment of cancer.

An Aluminum Triflate‐Catalyzed Intramolecular Reaction Sequence Toward Concise Construction of the Tetrahydropyrido[1,2‐a]indol‐6‐one Skeleton

AbstractAn aluminum triflate‐catalyzed intramolecular reaction sequence involving protonation and Mannich‐like nucleophilic addition of indoles toward the concise construction of the tetrahydropyrido[1,2‐a]indol‐6‐one skeleton is reported. This new reaction pattern employs a carbon atom as nucleophile to form a CC bond which bears one or even two quaternary carbons and leads to the dearomatization of indoles with high atom economy.magnified image

Nucleophilic addition of indole and its derivatives to ?-aroylacrylic acids

Condensation of Β-benzoyl- and Β-toluylacrylic acids with indole and its derivative gave Β-benzoyl- and Β-toluyl-α-(3-indolyl)propionic acids and their derivatives.