22675-83-8

Upstream product

• 15875-74-8 N-(4-methoxybenzylidene)-2-methylpropan-2-amine 
• 75-64-9 tert-butylamine 
• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 97-93-8 triethylaluminum 
• 75-24-1 trimethylaluminum 

Downstream Products

• 15875-74-8 N-(4-methoxybenzylidene)-2-methylpropan-2-amine 
• 40117-28-0 N-(4-methoxy)benzylidene-t-butylamine N-oxide 
• 15875-74-8 (E)-tert-butyl[(4-methoxyphenyl)methylidene]amine 
• 335596-11-7 N-tert-butyl-4-methoxy-N-(4-methoxy-benzyl)-benzamide 
• 573975-35-6 N-(4-methoxybenzyl)-N-tert-butyl-2-oxopropionamide 
• 573975-02-7 N-(p-methoxybenzyl)-N-tert-butyl-2-oxopropionamide tosylhydrazone 
• 22246-66-8 6-methoxy-2,3-dihydro-isoindol-1-one 
• 22675-85-0 tert-butyl[(4-methoxyphenyl)methyl]amine hydrochloride 
• 1394173-08-0 C₁₆H₂₃NO₃ 
• 1612841-65-2 N-(tert-butyl)-N-(4-methoxybenzyl)methacrylamide 

Relevant academic research and scientific papers

Pathways of the reaction between N,N-disubstituted propargylic amines and cationic zirconium complexes

The reaction of N-tert-alkyl-substituted propargylic amines with trialkylalanes in the presence of 20 mol.% Cp2ZrCl2 was studied. The pattern of the products depended on the nature of substituents at the nitrogen atom. N-tert-Alkyl-N-arylmethyl-substituted propargylic amines when reacted in CH2Cl2 aff ord a mixture of N-tert-alkyl-N-(arylmethyl)alkylamines and N-tertalkyl-N-(arylmethyl)amines at ratios from {2: 3 to {3: 2 in total yield of 70–95%. In hexane, N-tert-alkyl-N-(arylmethyl)amines are produced selectively. N-Alkyl-N-tert-alkyl-substituted propargylic amines similar to N-isoalkyl-substituted ones underwent a Zr-promoted hydride transfer to aff ord (2E)-alkenylamines in good yield (58–69%).

Structure-Activity Relationship and Biological Investigation of SR18292 (16), a Suppressor of Glucagon-Induced Glucose Production

Despite a myriad of available pharmacotherapies for the treatment of type 2 diabetes (T2D), challenges still exist in achieving glycemic control. Several novel glucose-lowering strategies are currently under clinical investigation, highlighting the need f

Heterometallic Mg?Ba Hydride Clusters in Hydrogenation Catalysis

Reaction of a MgN“2/BaN”2 mixture (N“=N(SiMe3)2) with PhSiH3 gave three unique heterometallic Mg/Ba hydride clusters: Mg5Ba4H11N”7 ? (benzene)2 (1), Mg4Ba7H13N“9 ? (toluene)2 (2) and Mg7Ba12H26N”12 (3). Product formation is controlled by the Mg/Ba ratio and temperature. Crystal structures are described. While 3 is fully insoluble, clusters 1 and 2 retain their structures in aromatic solvents. DFT calculations and AIM analyses indicate highly ionic bonding with Mg?H and Ba?H bond paths. Also unusual H????H? bond paths are observed. Catalytic hydrogenation with MgN“2, BaN”2 and the mixture MgN“2/BaN”2 has been studied. Whereas MgN“2 is only active in imine hydrogenation, alkene and alkyne hydrogenation needs the presence of Ba. The catalytic activity of the MgN”2/BaN“2 mixture lies in general between that of its individual components and strong cooperative effects are not evident.

Regio- and Enantioselective Intramolecular Amide Carbene Insertion into Primary C-H Bonds Using Ru(II)-Pheox Catalyst

We have established a method for the highly regio- and enantioselective functionalization of tert-butyl groups via intramolecular amide carbene insertion into C-H bonds, yielding γ-lactams with 91% ee in up to 99% yield. This reaction uses a ruthenium(II) phenyl oxazoline (Ru(II)-Pheox) complex. The catalytic intramolecular carbene transfer reaction to the primary C-H bond proceeds rapidly and selectively compared to that with secondary C-H, benzylic secondary C-H, tert-C-H, or sp2C-H bonds in the presence of 1 mol % Ru(II)-Pheox catalyst. This is the first example of a catalytic carbenoid insertion into an unactivated tert-butyl group with enantiocontrol at the carbenoid carbon.

Electrochemical Approach for Direct C-H Phosphonylation of Unprotected Secondary Amine

Direct α-phosphonylation of an unprotected secondary amine in a single step is of practical importance to amino phophophates. However, this protocol is limited due to the high redox barrier of unprotected amine. In this paper, we report C-H phosphonylation of an unprotected secondary amine via an electrochemical approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target molecules with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization.

Photocatalyzed cascade Meerwein addition/cyclization of: N -benzylacrylamides toward azaspirocycles

A visible-light-induced cascade Meerwein addition/cyclization of alkenes involving C-F bond cleavage was developed. This method offers a rapid access to azaspirocyclic cyclohexadienones from N-benzylacrylamides via C-F bond cleavage applying H2O as an external oxygen source, allowing for the incorporation of various aromatic moieties originating from aryldiazonium salts.

Synthetic method and application of azaspirocyclohexadienone

The invention discloses a method of synthesizing aryl substituted azaspirocyclohexadienone by aromatizing a visible light induced (N)-benzylacrylamide compound and diazonium salt of fluoboric acid toform a ring. The synthesized target compound has the structure as shown in the formula as described in the specification. A preparation method comprises the following steps: carrying out a reaction bytaking the (N)-benzylacrylamide compound and the diazonium salt as a reaction primer for 18 h, Ru(bpy)3Cl2 as a catalyst, K2CO3 as alkali and DMF (N,N-dimethylformamide) as a solvent in a nitrogen environment, wherein the reaction temperature is room temperature; and carrying out column chromatography or thin-layer chromatographic separation and purification on the product through washing, concentration and the like to obtain the target product azaspirocyclohexadienone. The synthesizing reaction is simple to operate, the adopted free radical source is low in price and easy to obtain, the reaction system is mild and environmentally friendly, and the method is high in selectivity, simple in condition and high in yield, and has a huge popularization and application value.

LiAlH4: From Stoichiometric Reduction to Imine Hydrogenation Catalysis

Imine-to-amine conversion with catalytic instead of stoichiometric quantities of LiAlH4 is demonstrated (85 °C, catalyst loading≥2.5 mol %, pressure≥1 bar). The effects of temperature, pressure, solvent, and catalyst modifications, as well as the substrate scope are discussed. Experimental investigations and preliminary DFT calculations suggest that the catalytically active species is generated in situ: LiAlH4+Ph(H)C=NtBu→LiAlH2[N(tBu)CH2Ph]2. A cooperative mechanism in which Li and Al both play a prominent role is proposed.

Improved Buchner reaction selectivity in the copper-catalyzed reactions of ethyl 3-arylmethylamino-2-diazo-3-oxopropanoates

Ethyl 3-alkyl(arylmethyl)amino-2-diazo-3-oxopropanoates (diazo amidoacetates) generate generally both cyclohepta[c]pyrrolones (Buchner products) and β-lactams (1,4-insertion products), and show obvious N-substituent-controlled chemoselectivity between the intramolecular Buchner reaction and aliphatic 1,4-C-H insertion under the catalysis of copper salts. The less steric N-alkyl substituents in the amide moiety generally favor the aliphatic 1,4-C-H insertion, while the more steric N-alkyl substituents generally favor the Buchner reaction. Compared with rhodium and ruthenium-catalyzed conditions, the current copper-catalyzed conditions improved the Buchner reaction selectivity of ethyl 3-alkyl(arylmethyl)amino-2-diazo-3-oxopropanoates.

Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: Efficient construction of 2-azaspiro[4.5]decanes

An efficient intramolecular dearomative cyclization via visible light-induced photoredox catalysis allows for a highly regioselective dearomative cyclization of α-bromo-N-benzyl-alkylamides to construct 2-azaspiro[4.5]decanes in the presence of an iridium catalyst.