40926-90-7

Upstream product

• 41764-74-3 3,4-dimethoxybenzohydrazide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-07-2 Veratric acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 52751-63-0 1,3-di-(3,4-dimethoxyphenyl)-1,3-propanedione 
• 80370-28-1 1-(3,4-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 

Downstream Products

• 37527-66-5 3,4-dimethoxyphenylisocyanate 
• 35162-34-6 N-methyl-3,4-dimethoxyaniline 
• 46809-30-7 3-(3,4-dimethoxy-phenyl)-1-methyl-imidazolidin-4-one 
• 1447648-74-9 1-((1-(1H-indazol-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-3-(3,4-dimethoxyphenyl)urea 
• 1432579-07-1 1-(3,4-dimethoxyphenyl)-3-(2-propynyl)urea 

Relevant academic research and scientific papers

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition

A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.

Synthesis of Acyl Azides from 1,3-Diketones via Oxidative Cleavage of Two C-C Bonds

A metal-free PhI(OAc)2-mediated method for the synthesis of acyl azides through oxidative cleavage of 1,3-diketones is described. This method is shown to have a broad substrate scope, providing a useful tool for multiproduct synthesis in a single procedure. A possible reaction pathway is proposed based on mechanistic studies.

Copper-catalyzed N[sbnd]H/S[sbnd]H functionalization: A strategy for the synthesis of benzothiadiazine derivatives

A copper-mediated N[sbnd]S bond-forming reaction via N[sbnd]H/S[sbnd]H activation is described. This reaction occurs under mild conditions with high efficiency, step economy, and tolerates a wide variety of functional groups, providing an efficient means of accessing biologically important 1,2,4-benzothiadiazin-3(4H)-ones.

Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1, 2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 μM. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 μM, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization.

Synthesis of N-methylphenanthridinone derivatives fused with a silacyclohexane ring by radical reaction using tributyltin hydride

Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6- and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dimethyl-2-silatetralin-6-carboxamides (14) produced N-methylphenanthridinone deivatives (17) as each sole product, in which cyclization occurred at 5-position of 2-silatetralin moiety.

A new facile and rapid synthesis of acyl azides under solvent-free conditions

A rapid and simple method for the preparation of acyl azides is described. The reaction is carried out under solvent-free conditions from the reaction of acid chlorides with sodium azide supported on silica gel.

ONE-FLASK SYNTHESIS OF ACYL AZIDES FROM CARBOXYLIC ACIDS; A FACILE ROUTE TO IMINOPHOSPHORANES

Carboxylic acids react with a mixture of N-chlorosuccinimide, triphenylphosphine and sodium azide at -30 deg C to form acyl azides in high yields.When two equivalents of triphenylphosphine are applied and the temperature allowed to raise, the reaction yields directly α-carbonyl stabilized iminophosphoranes via Staudinger reaction of the phosphine with the intermediate acyl azide.Key words: Iminophosphoranes; acyl azides; one-flask synthesis.

Modified Pyridinium Chlorochromate Oxidation of Aldehydes to Carbamoyl Azides/Acyl Azides or Carboxylic Acids

Aldehydes are transformed into carbamoyl azides/acyl azides by pyridinium chlorochromate in the presence of sodium azide.Comparable oxidations modified with sodium cyanide generate carboxylic acids from simple aliphatic aldehydes whereas conjugated aldehydes are undeactive.