95104-17-9

Upstream product

• 61-70-1 N-methyl-2-indolinone 
• 536-74-3 phenylacetylene 
• 128351-01-9 1-methyl-2-(2-phenylethynyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 75833-63-5 2-iodo-1-methyl-1H-indole 
• 13146-23-1 copper(I) phenylacetylenide 
• 156137-02-9 2-bromo-1-methyl-1H-indole-3-carboxyaldehyde 

Downstream Products

• 1239320-94-5 C₃₀H₂₆N₂O₂ 
• 1380545-06-1 (5-methyl-5,7-dihydroindolo[2,3-b]carbazol-6-yl)(phenyl)methanone 
• 95104-18-0 2-phenyl-9-methyl-γ-carboline N-oxide 
• 95104-16-8 3-formyl-2-phenylethynyl-1-methylindole oxime 

Relevant academic research and scientific papers

Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement

Rearrangement reactions in organic chemistry are attractive strategies to build efficiently complex scaffolds, in just one step, from simple starting materials. Among them, aryl migrations are certainly one of the most useful and straightforward rearrangement for building attractive carbon-carbon bonds. Of note, anionic aryl migration reactions have been largely described compared to their radical counterparts. Recently, visible-light catalysis has proven its efficiency to generate such radical rearrangements due to the concomitant loss of a particle (often CO2 or SO2), which is the driving-force of the reaction. Here, we disclose a Smiles-type rearrangement, triggered by a phosphorus-containing unit (arylphosphoramidate), therefore called "phospho-Smiles"rearrangement, allowing a Csp2-Csp2 bond formation thanks to a 1,4-aryl migration reaction. In addition, combining this approach with a radical hydroamination/amination reaction produces an amination/phospho-Smiles cascade particularly attractive, for instance, to investigate the synthesis of the phthalazine core, a scarcely described scaffold of interest for medicinal chemistry projects.

Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable

Transition-Metal-Free Access to Pyridocarbazoles from 2-Alkynylindole-3-carbaldehydes via Azomethine Ylide

An efficient approach for the synthesis of functionalized tetrahydro-pyrido/quinolinocarbazoles from 2-alkynylindole-3-carbaldehydes and l-proline utilizing a metal-free decarboxylative cyclization, ring expansion, and ring contraction strategy via the ge

Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes

An environmentally benign Au(III)-catalyzed regio- and stereoselective domino synthesis of oxazolo fused pyridoindoles 7a-v and benzofurooxazolo pyridines 8a-n by the reaction of o-alkynylaldehydes 4a-t and 5a-k with (S)-phenylglycinol 6a and (R)-phenylglycinol 6b under mild reaction conditions using water as reaction medium is reported. The reaction proceeded via selective C-N bond formation on the more electrophilic alkynyl carbon through 6-endo-dig cyclization. The reaction tolerates a wide variety of functional groups. The developed chemistry has been successfully extended for the synthesis of a diverse class of carbolines and benzofuro[3,2-c]pyridines using corresponding ester hydrochlorides of serine, threonine, and cystine as a nitrogen source.

Rapid access to amino-substituted quinoline, (Di)benzofuran, and carbazole heterocycles through an aminobenzannulation reaction

(Chemical Equation Presented) The use of a powerful aminobenzannulation reaction has been applied for the synthesis of amino-substituted quinolines, dibenzofurans, and carbazoles. The precursors are heterocycles bearing a methyl ketone group ortho to an i

Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes

A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes using cat. PdCl

Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes

A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes with PdCl2(PPh3)2/CuI as the catalyst readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to β- and γ-carbolines by either copper-catalyzed or thermal processes.