40078-73-7

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 100-52-7 benzaldehyde 
• 455-16-3 p-toluenesulfonyl fluoride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 2411-77-0 N-methyl-4-phenylimidazole 
• 1006-68-4 5-phenyloxazole 
• 670-95-1 4-Phenylimidazole 

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.

Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst

The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.

A Mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles

A facile and mild synthesis of 4-tosyl-4,5-dihydrooxazoles is described. The reaction between tosyl methyl isocyanide (TosMIC) and cinnamic or aromatic aldehydes is catalyzed by triethylamine, affording trans-5-styryl- or 5-aryl-4-tosyl-4,5-dihydrooxazole

A Two-Step Synthesis of Imidazoles from Aldehydes via 4-Tosyloxazolines

Imidazoles with substituents in the 4- and 4,5-positions were prepared by heating 4-tosyloxazolines in saturated methanolic ammonia.Similar treatment of these oxazolines with monoalkylamines regioselectively affords 1,4-disubstituted imidazoles.When oxazolines bearing an ethyl group at the 4-position were heated with alkylamines, however, a regioisomeric mixture of di- or trisubstituted imidazoles was produced.These reactions proceed via an intermolecular condensation of α-amino ketones and amidines or intramolecular cyclization of α-amidino ketone intermediates, respectively.

The Asymmetric Aldol Reaction of Tosylmethyl Isocyanide and Aldehydes Catalyzed by Chiral Silver(I) Complexes

The asymmetric aldol reaction of tosylmethyl isocyanide and aldehydes in the presence of 1 mol percent of chiral silver(I) catalysts gave optically active 5-alkyl-4-tosyl-2-oxazolines (up to 86percent ee), which were converted to optically active α-alkyl-β-(N-methylamino)ethanols by LiAlH4 reduction.