886499-20-3Relevant academic research and scientific papers
Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
, p. 1553 - 1558 (2021/02/26)
Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles
Giustiniano, Mariateresa,Pelliccia, Sveva,Sangaletti, Luca,Meneghetti, Fiorella,Amato, Jussara,Novellino, Ettore,Tron, Gian Cesare
supporting information, p. 4264 - 4268 (2017/10/11)
A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Br?nsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.
Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Bronsted acid catalysis
Dhiman, Seema,Ramasastry
supporting information, p. 557 - 560 (2015/01/09)
An efficient relay catalytic process involving Au(i)/Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel-Crafts-type reaction generating functionalized cyclopenta[b]indoles. This journal is
Diastereoselective construction of highly functionalized tetrahydroquinolinoisoxazole scaffolds via intramolecular nitrone cycloaddition
Bakthadoss, Manickam,Devaraj, Anthonisamy
, p. 3954 - 3960 (2015/06/08)
A novel strategy towards the construction of highly diversified tetrahydroquinolinoisoxazole frameworks with high diastereoselectivity via intramolecular 1,3-dipolar nitrone cycloaddition reaction is described for the first time. All the synthesized tetrahydroquinolinoisoxazoles are new and obtained in excellent yields under catalyst free condition.
Broensted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans
Kuznetsov, Alexey,Makarov, Anton,Rubtsov, Aleksandr E.,Butin, Alexander V.,Gevorgyan, Vladimir
, p. 12144 - 12153 (2014/01/06)
Broensted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including -OMe, -CO2Cy, and -Br. The resulting indoles can easily be transformed into diverse scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an α,β-unsaturated ketone moiety at the C-2 position.
