50625-49-5

Upstream product

• 1673-47-8 3-chlorobenzhydrazide 
• 587-04-2 m-Chlorobenzaldehyde 
• 84553-20-8 α,α-dichloro-m-chloroacetophenone 
• 6297-12-7 1,3-bis(3-chlorophenyl)-1,3-propanedione 
• 535-80-8 3-chlorobenzoate 
• 93507-06-3 C₁₀H₉ClO₄ 
• 37156-55-1 2,4-dinitrophenyl 3-chlorobenzoate 
• 618-46-2 m-Chlorobenzoyl chloride 

Downstream Products

• 2150-89-2 (3-chlorophenyl) carbamic acid ethyl ester 
• 94398-04-6 N-benzoyl-N'-(3-chloro-phenyl)-urea 
• 54964-90-8 N-(3-chlorophenyl)-N'-(2-methoxyphenyl)-urea 
• 72802-45-0 1-(3-chlorophenyl)-3-cyclohexylurea 
• 13208-32-7 1-(3-chlorophenyl)-3-(4-chlorophenyl)urea 
• 13142-01-3 1-(3-chlorophenyl)-3-(4-nitrophenyl)urea 
• 13208-31-6 N_.N'-Di-(m-chlor-phenyl)-harnstoff 
• 13141-93-0 N-(4-ethoxy-phenyl)-N'-(3-chloro-phenyl)-urea 
• 13142-09-1 N-(4-bromophenyl)-N'-(3-chlorophenyl)-urea 
• 13208-28-1 N-(3-chlorophenyl)-N'-(2,4-dimethylphenyl)-urea 
• 13143-35-6 1-(3-chlorophenyl)-3-(m-tolyl)urea 
• 13208-21-4 N-(2-chloro-phenyl)-N'-(3-chloro-phenyl)-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.

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.

Pathways in the Degradation of Geminal Diazides

The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.

Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles

An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).

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 and biological activity of some novel N-aryl-nprime;-[5-(pyrid-4- yl)-1,3,4-thiadiazol-2-yl]ureas

With the aim of searching for biologically active urea compounds, a series of new N-aryl-N'-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]ureas have been designed and synthesized. Their structures were confirmed by IR, 1H NMR, and elemental analysis. The crystal

Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization

A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.

Oxidation of aldehydes to acyl azides using triazidochlorosilane (TACS)-active manganese dioxide reagent

Triazidochlorosilane (TACS)-active manganese dioxide is a new and versatile system for the efficient oxidation of aldehydes to the corresponding acyl azides at 0°C, in dichloromethane.