cas 496-42-4, 2-(2-Aminoethyl)indole | Articles data

Articles about 496-42-4Total 8 be found

Au(I)-Catalyzed Pictet-Spengler Reactions All around the Indole Ring
Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4, or the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.
Milcendeau, Pierre,Zhang, Zhenhao,Glinsky-Olivier, Nicolas,Van Elslande, Elsa,Guinchard, Xavier
p. 6406 - 6422
(2021/05/29)

A Novel Sc(OTf)3-Catalyzed (2+2+1)-Cycloannulation/Aza-Friedel–Crafts Alkylation Sequence toward Multicyclic 2-Pyrrolines
The rapid assembly of molecular complexity continues to be at the forefront of novel reaction development. In the pursuit of that goal, we herein report a novel Sc(OTf)3-catalyzed, one-pot multicomponent reaction that furnishes complex multicyclic 2-pyrrolines with excellent overall yields and perfect diastereocontrol. This process is based on our previously established (2+2+1)-cycloannulation of in situ generated 1-azaallyl cations, 1,3-dicarbonyls and primary amines. The newly formed and highly reactive aminal moiety is readily substituted with indoles and pyrroles both as external and internal π-nucleophiles to provide densely functionalized N-heterocycles with four new σ-bonds and two vicinal quaternary stereogenic centers. In addition, DFT calculations have been conducted to further characterize the intermediate 1-azaallyl cations.
Schlegel, Marcel,Coburger, Peter,Schneider, Christoph
supporting information
p. 14207 - 14212
(2018/09/14)

An Enantio- and Diastereoselective Mannich/Pictet–Spengler Sequence To Form Spiro[piperidine-pyridoindoles] and Application to Library Synthesis
A new tandem strategy based on a Mannich/Pictet–Spengler sequence has been developed and applied to the synthesis of a new small library (14 examples) of privileged compounds based on the spiro[piperidine-pyridoindole] core. The sequence proceeds by a diastereoselective Pictet–Spengler cyclization after condensation of several tryptamine derivatives with three novel piperidin-4-ones containing the fluorinated substituents F, CF3and SF5. The piperidin-4-ones were synthesized from readily available starting materials by an enantioselective multi-component organocatalytic Mannich reaction.
Riesco-Domínguez, Alejandra,van der Zwaluw, Nick,Blanco-Ania, Daniel,Rutjes, Floris P. J. T.
p. 662 - 670
(2017/02/05)

Diastereodivergent pictet-spengler cyclization of bicyclic N-acyliminium ions: Controlling a quaternary stereocenter
The diastereoselectivity of the Pictet-Spengler cyclization of bicyclic N-acyliminium ions that contain a 3-azabicyclo-[n.3.0]alkane core and an electron-rich ?-nucleophilic moiety, such as an indol-2-yl, indol-3-yl, 1-methylpyrrol-2-yl, or 3,5-dimethoxyphenyl group, was examined. The N-acyliminium ions were generated by protonation of the corresponding enamides or hemiaminals, which were derived from imides. Control of the quaternary stereocenter created at the newly formed ring junction was achieved in a diastereodivergent manner by fine-tuning the reaction conditions, which determined whether the reaction proceeded under kinetic or thermodynamic control. Mechanistic studies indicated that a retro-Pictet-Spengler reaction pathway is involved in the equilibration process.
De Carn-Carnavalet, Benot,Krieger, Jean-Philippe,Follas, Benot,Brayer, Jean-Louis,Demoute, Jean-Pierre,Meyer, Christophe,Cossy, Janine
supporting information
p. 1273 - 1282
(2015/03/04)

Thiourea-catalyzed enantioselective iso-pictet-spengler reactions
A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-prot
Lee, Yunmi,Klausen, Rebekka S.,Jacobsen, Eric N.
p. 5564 - 5567
(2011/12/03)

Dopamine receptor ligands. Part 18: Modification of the structural skeleton of indolobenzazecine-type dopamine receptor antagonists
On the basis of the D1/5-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca2+ assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f] benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.
Robaa, Dina,Enzensperger, Christoph,El Din Abul Azm, Shams,El Khawass, El Sayeda,El Sayed, Ola,Lehmann, Jochen
supporting information; experimental part
p. 2646 - 2650
(2010/08/19)

Regiospecific preparation of γ-carbolines and pyrimido[3,4-a]indole derivatives by intramolecular ring-closure of heterocumulene-substituted indoles
Compounds resulting from the aza-Wittig reaction of iminophosphorane derived from 2-(2-azidoethyl)indole and carbon disulfide, diphenylketene, aldehydes and acyl chlorides undergo ring-closure under acidic, basic and thermal conditions to give either dihydro γ-carbolines or dihydropyrimido[3,4-a]indoles in a completely regiospecific fashion. The mode of cyclization strongly depends on the cyclizating agents as well as the nature of the reagent. The related carbodiimides 9 undergo regiospecific cyclization to give dihydropyrimido[3,4-a]indoles under acidic, basic or thermal conditions.
Molina, Pedro,Alcantara, Julian,Lopez-Leonardo, Carmen
p. 5833 - 5844
(2007/10/03)

Regiospecific Intramolecular Ring-Closure of Heterocumulene-Substituted Indoles: Formation of γ-Carbolines and Pyrimidoindoles.
2-(Indol-2-yl)ethyl heterocumulenes undergo ring-closure under acid, basic and thermal conditions to give either dihydro γ-carbolines or dihydropyrimidoindoles in a completeley regiospecific fashion.The mode of cyclization strongly depends on the c
Molina, Pedro,Alcantara, Julian,Lopez-Leonardo, Carmen
p. 953 - 956
(2007/10/02)