38018-60-9

Upstream product

• 104-94-9 4-methoxy-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 18982-54-2 o-bromobenzyl alcohol 

Downstream Products

• 1133378-60-5 (2S,3S)-2-(2-bromophenyl)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydropyridine-3-carbaldehyde 
• 1104927-23-2 methyl 2-(9-anthrylmethoxy)-3-(4-methoxyphenylamino)-3-(2-bromophenyl)-2-phenylpropanoate 
• 1104927-39-0 methyl 2-(9-anthrylmethoxy)-3-(4-methoxyphenylamino)-3-(2-bromophenyl)-2-(4-methoxyphenyl)propanoate 
• 1393689-02-5 tert-bButyl 2-(2-(4-methoxyphenyl)isoindolin-1-yl)acetate 

Relevant academic research and scientific papers

Arene diruthenium(II)-mediated synthesis of imines from alcohols and amines under aerobic condition

The utility and selectivity of the newly synthesized dinuclear arene Ru(II) complex were demonstrated towards the synthesis of imines from coupling of alcohols and amines in the aerobic condition. Analytical and various spectral methods have been used to establish the unprecedented formation of the new thiolato-bridged dinuclear ruthenium complex. The molecular structure of the titled complex was evidenced with aid of X-ray crystallographic technique. A wide range of imines were obtained in good-to-excellent yields up to 98% and water as the by-product through an acceptorless dehydrogenative coupling of alcohols with amines. The catalytic reaction operated a concise atom economical without any oxidant with 1 mol% of the catalyst load. Further, the role of base, solvent and catalyst loading of the coupling reaction has been investigated. A plausible mechanism has been described and was found to proceed via the formation of an aldehyde intermediate. Short synthesis of antibacterial drug N-(salicylidene)-2-hydroxyaniline illustrated the utility of the present protocol.

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.

Manganese-Catalyzed Electrochemical Tandem Azidation-Coarctate Reaction: Easy Access to 2-Azo-benzonitriles

A one-pot cascade transformation consisting of an electrochemically driven azidation of 2H-indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.

Oxidative cross-dehydrogenative coupling (CDC)viaC(sp2)-H bond functionalization:tert-butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2H-indazoles with aldehydes/benzyl alcohols/styrenes

An efficient, cost-effective, transition-metal-free, oxidative C(sp2)-H/C(sp2)-H cross-dehydrogenative couplingviaa C(sp2)-H bond functionalization protocol for the regioselective direct C-3 acylation/benzoylation of subst

Enantioselective Direct anti-Selective Mannich-type Reactions Catalyzed by 3-Pyrrolidinecarboxylic Acid in the Presence of Potassium Carbonate: Addition of Potassium Carbonate Improves Enantioselectivities

Mannich-type reactions of cyclohexanone and related six-membered-ring ketones with N-p-methoxyphenyl-protected imines of arylaldehydes catalyzed by 3-pyrrolidinecarboxylic acid in the presence of K2CO3 that afford anti-isomers of the Mannich products with

Bu4NI-catalyzed, oxidative C(sp2)-C(sp3)cross dehydrogenative coupling for the regioselective direct C-3 benzylation of 2: H -indazoles

A Bu4NI-catalyzed, DTBP-promoted, regioselective C(sp2)-C(sp3) cross dehydrogenative coupling (CDC) protocol for the direct C-3 benzylation of 2H-indazoles is reported. The metal-free protocol is operationally simple and proceeds mechanistically via the g

Rearrangement Reactions in Aza-Vinylogous Povarov Products: Metal-Free Synthesis of C3-Functionalized Quinolines and Studies on their Synthetic Application

Several types of C4-functionalized 4-alkyl-2-aryl-1,2,3,4-tetrahydroquinolines underwent rearrangement of their functional groups to C3, with concomitant aromatization, by simple reflux in 1,2-dichlorobenzene. The functional groups that were shown to undergo the C4 to C3 migration were –CH=CH-Z (where Z = CO2Et, CN, NO2, COCH3, CH2OH) and –CH=C(Y)–Z (where Y = CN and Z = CO2Et or Y = Z = CN). On the other hand, the dimethylhydrazono group failed to migrate under thermal conditions but was shown to undergo a smooth dehydrogenation/C4 to C3 rearrangement/ dehydrogenation sequence at room temperature in the presence of DDQ, with a broad scope that includes 4-alkyl-2-aryl- and 2-acyl-1,2,3,4-tetrahydroquinolines. We also report a computational and experimental study of the mechanism of both reactions, which supports an unusual intramolecular aza-ene pathway. The ready availability by this method of 2,3-difunctionalized quinolines allowed the simple preparation of fused heterocyclic systems derived from the pyrrolo[3,4-b]quinoline framework, using both reductive and non-reductive domino processes.

One-pot sequential multicomponent reaction between: In situ generated aldimines and succinaldehyde: Facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles

An efficient sequential multi-component method for the synthesis of N-Arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and in situ generated Ar/H

Direct Acyl Radical Addition to 2 H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids

A direct acyl radical addition to 2H-indazoles has been achieved for the first time, where the less-aromatic quinonoid 2H-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2H-indazoles, the current method utilizes the radical acceptability of 2H-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-acyl-2H-indazoles with three points of structural diversification in 25%-83% yields.

One-Pot Catalytic Approach for the Selective Aerobic Synthesis of Imines from Alcohols and Amines Using Efficient Arene Diruthenium(II) Catalysts under Mild Conditions

A green and efficient catalytic approach for the selective synthesis of imines in air at room temperature was achieved with the aid of newly synthesised diruthenium(II) complexes [(η6-p-cymene)2Ru2Cl2(μ-L)] containing substituted 1,2-diacylhydrazine ligands. All the new complexes were fully characterised by analytical and spectroscopic techniques. The solid-state structure of a representative complex was solved by single-crystal X-ray diffraction analysis. The diruthenium(II) complexes also enable the selective aerobic oxidation of alcohols to aldehydes. The catalytic reaction operates in the presence of air as a green and cheap oxidant, and releases water as the only by-product. A plausible mechanism is proposed for the imine formation, which is believed to proceed via an aldehyde intermediate.