356531-15-2

Upstream product

• 104-94-9 4-methoxy-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1234560-03-2 C₂₂H₁₈BrNO₄ 
• 1393689-02-5 tert-bButyl 2-(2-(4-methoxyphenyl)isoindolin-1-yl)acetate 
• 78317-83-6 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence

N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.

Ruthenium-Catalyzed Selective Hydroboration of Nitriles and Imines

Ruthenium-catalyzed hydroboration of nitriles and imines is attained using pinacolborane with unprecedented catalytic efficiency. Chemoselective hydroboration of nitriles over esters is also demonstrated. A simple [Ru(p-cymene)Cl2]2 complex (1) is used as a catalyst precursor, which upon reaction with pinacolborane in situ generates the monohydrido-bridged complex [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] 2. Further oxidative addition of pinacolborane to intermediate 2 leading to the formation of mononuclear ruthenium hydride species is suggested. Mass spectral analysis of the reaction mixture and independent experiments with phosphine-ligated ruthenium complexes indicated the involvement of mononuclear ruthenium intermediates in the catalytic cycle. Consecutive intramolecular 1,3-hydride transfers from the ruthenium center to coordinated nitrile and boronate imine ligands, leading to the reduction and resulting in the formation of diboronate amines, are proposed as a plausible reaction mechanism.

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.

A tandem Heck-aza-Michael addition protocol for the one-pot synthesis of isoindolines from unprotected amines

A palladacycle-catalyzed tandem Heck-intramolecular aza-Michael reaction protocol has been developed for the one-pot synthesis of 1-substituted isoindolines from N-unprotected 2-bromobenzylamines and acrylates with high yields.

Synthesis of N -arylisoindolin-1-ones via pd-catalyzed intramolecular decarbonylative coupling of N -(2-bromobenzyl)oxanilic acid phenyl esters

Ethyl and phenyl oxanilates were readily prepared from N-(2-bromobenzyl) anilines and oxalyl chloride monoethyl and monophenyl esters, respectively. It was found that the ethyl oxanilate survived in the presence of K 2CO3 in DMA at 120°C and underwent an intramolecular direct arylation using Pd(OAc)2-dppf, furnishing the 5,6-dihydrophenanthridine derivative. In contrast, the corresponding phenyl oxanilates decomposed upon exposure to K2CO3 in DMA at 120 C and were transformed into N-arylisoindolin-1-ones via Pd(OAc) 2-dppf-catalyzed intramolecular decarbonylative coupling. Except for the 4-methoxy-substituted oxanilic acid phenyl ester, other phenyl oxanilates possessing electron-withdrawing (NO2, Cl) and weak electron-donating (Me) substituents provided the N-arylisoindolin-1-ones in 43-80% yields.