126190-77-0

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 57830-48-5 2-((trifluoromethyl)thio)benzaldehyde 
• 929219-77-2 C₁₇H₁₅ClN₂O 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens

We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.

Ligandless Nickel-Catalyzed Ortho-Selective Directed Trifluoromethylthiolation of Aryl Chlorides and Bromides Using AgSCF3

A mild protocol for Ni-catalyzed trifluoromethylthiolation of aryl chlorides and bromides is described herein. The method utilizes AgSCF3 as an easily accessible nucleophilic trifluoromethylthiolating reagent and does not require any ligands or additives. Ortho-selectivity is achieved using a variety of directing groups such as imines, pyridines, and oxazolines for 24 examples in up to 95% yield.

Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free α-amino phosphonic acids in highly enantioenriched form. Copyright

Regioselective cyclomanganation of Schiff bases. An unexpected effect of chloro substituents

The synthesis of new metallacycles of benzyl-benzylidene-amines by using [MnMe(CO)5] as metallating agent is reported. The results described suggest that cyclomanganation takes place by the formation of a four-centered transition state, involving the C-H and Mn-Cacetyl bonds, in the acetyl coordination complex formed in the first step of the reaction. In this paper we describe the synthesis of new metallacycles by the cyclomanganation reaction of benzyl-benzylidene-amines by using [MnMe(CO)5] as metallating agent. These ligands can undergo metallation on different aromatic carbon atoms but no important differences have been found in the regioselectivity of the process, that can be related to the electronic effect of the substituents, and in all the cases studied the endo-cyclomanganated complexes of para-substituted imines have been obtained. The corresponding exo-metallacycles were obtained by reaction of [MnMe(CO)5] on the imine 2,6-Cl2C6H3CH=NCH2Ph and 2,4,6-Me3C6H2CH=NCH2Ph, derived from 2,6-dichlorobenzaldehyde and 2,4,6-trimethylbenzaldehyde, respectively. The results described suggest that the mechanism of the cyclomanganation is similar to that of cyclopalladation and it can be proposed that cyclomanganation takes place by the formation of a four-centered transition state, involving the C-H and Mn-Cacetyl bonds, in the acetyl coordination complex formed in the first step of the reaction.