86489-64-7

Upstream product

• 93-07-2 Veratric acid 
• 100-46-9 benzylamine 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 1521-41-1 veratramide 
• 100-51-6 benzyl alcohol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 83735-51-7 3,4-dimethoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester 

Downstream Products

• 81819-71-8 N-benzyl-3,4-dihydroxy-benzamide 
• 1144526-59-9 5-benzyl-1,2-dimethoxydibenzo[cd,f]indol-4(5H)-one 
• 1613320-07-2 2-(benzylcarbamoyl)-4,5-dimethoxyphenyl 4-chlorobenzoate 

Relevant academic research and scientific papers

Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines

A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.

N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation

A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is

Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene

Cyrene as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.

Nickel-Catalyzed Phosphine Free Direct N-Alkylation of Amides with Alcohols

Herein, we developed an operational simple, practical, and selective Ni-catalyzed synthesis of secondary amides. Application of renewable alcohols, earth-abundant and nonprecious nickel catalyst facilitates the transformations, releasing water as byproduct. The catalytic system is tolerant to a variety of functional groups including nitrile, allylic ether, and alkene and could be extended to the synthesis of bis-amide, antiemetic drug Tigan, and dopamine D2 receptor antagonist Itopride. Preliminary mechanistic studies revealed the participation of a benzylic C-H bond in the rate-determining step.

Hansch analysis of veratric acid derivatives as antimicrobial agents

The synthesis, characterization and antimicrobial evaluation of a new series of veratric acid derivatives are presented. Preliminary in vitro antimicrobial activity of the title compounds was assessed against a panel of microorganisms including Gram-positive and Gram-negative bacteria and fungi. Some of the veratric acid derivatives exhibited significant in vitro antimicrobial activity. QSAR investigation applied to find a correlation between different physicochemical parameters of the veratric acid derivatives and their antimicrobial activity indicated the importance of topological parameters in describing the antimicrobial activity.

N-Benzylbenzamides: A new class of potent tyrosinase inhibitors

A series of potent inhibitors of tyrosinase and their structure-activity relationships are described. N-Benzylbenzamide derivatives (1-21) with hydroxyl(s) were synthesized and tested for their tyrosinase inhibitory activity. With this series, compound 15 provided a potent tyrosinase inhibition: it effectively inhibited the oxidation of l-DOPA catalyzed by mushroom tyrosinase with an IC50 of 2.2 μM.

Improved microwave oven synthesis of amides and imides promoted by imidazole; convenient transport agent preparation

Microwave dielectric loss heating without solvent or support yields amides and imides from aromatic and sterically hindered acids in the presence of imidazole in good to excellent yields under mild irradiation conditions.

DIPHOSPHORUS TETRAIODIDE AS A NEW MILD CONDENSING AGENT FOR THE SYNTHESIS OF AMIDES

In the presence of diphosphorus tetraiodide, a variety of weak carboxylic acids readily react with amines to form the corresponding amides in high yields.