130517-95-2

Upstream product

• 120-57-0 piperonal 
• 100-46-9 benzylamine 
• 495-76-1 piperonol 

Downstream Products

• 4720-73-4 1-(benzo[d][1,3]dioxol-5-yl)-N-benzylmethanamine 
• 54089-46-2 3-benzo[1,3]dioxol-5-yl-2-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-4-carbonitrile 
• 130517-99-6 (1-Benzo[1,3]dioxol-5-yl-but-3-enyl)-benzyl-amine 
• 1337933-89-7 4,5-bis(benzo[d][1,3]dioxol-5-yl)-1,3-dibenzyl-2-phenyl-4,5-dihydro-1H-imidazol-3-ium-5-carboxylate 
• 1437799-09-1 2-(benzo[d][1,3]dioxol-5-yl)-N-benzyl-2-(N-benzylacetamido)acetamide 

Relevant academic research and scientific papers

Lithium aluminum amides: New reagents for the synthesis of imines

Aldehydes (4 eqiv.) react under mild conditions with LiAL(NHR1)4 (1 eqiv.) to give the corresponding imines in 90% yield and no polymerization was observed upon reaction of aliphatic aldehyde 3.

Synthesis and anti-parasitic activity of N-benzylated phosphoramidate Mg2+-chelating ligands

A series of N-benzylated phosphoramidate esters, containing a 3,4-dihydroxyphenyl Mg2+-chelating group, has been synthesised in five steps as analogues of fosmidomycin, a Plasmodium falciparum 1-deoxy-1-D-xylulose-5-phosphate reductoisomerase (PfDXR) inhibitor. The 3,4-dihydroxyphenyl group effectively replaces the Mg2+-chelating hydroxamic acid group in fosmidomycin. The compounds showed very encouraging anti-parasitic activity with IC50 values of 5.6–16.4 μM against Plasmodium falciparum parasites and IC50 values of 5.2 – 10.2 μM against Trypanosoma brucei brucei (T.b.brucei). Data obtained from in silico docking of the ligands in the PfDXR receptor cavity (3AU9)5 support their potential as PfDXR inhibitors.

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.

Substituted 4-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a tandem imine addition-SNAr reaction

A tandem imine addition-SNAr annulation reaction has been developed as a new approach to the synthesis of 4-oxo-1,2,3,4- tetrahydroquinoline-3-carboxylic esters. A series of these structures has been generated by reacting selected imines with tert-butyl 2-fluoro-5- nitrobenzoylacetate. Structural variations in the final products are accomplished by changing the substituents on the imine and the alkyl group of the ester. The title compounds are isolated as their enols in 55-97% yield without the need for added base or catalysts. The synthesis of the starting materials as well as mechanistic studies and further synthetic conversions of the products are presented.

Ugi four-component reaction of alcohols: Stoichiometric and catalytic oxidation/MCR sequences

A new, simple, and efficient procedure for the one-pot Ugi four-component reaction of alcohols instead of aldehydes is described. Using a stoichiometric amount of IBX or only 1-2% of sodium 2-iodobenzenesulfonate in the presence of Oxone, a wide range of primary alcohols were oxidized to the aldehyde that were directly engaged in the Ugi four-component reaction to afford α-acetamidoamides in good to excellent yields.

Palladium-catalyzed aryl iodide carbonylation as a route to imidazoline synthesis: Design of a five-component coupling reaction

Take five: A new method employing aryl halide carbonylation to directly access heterocycles has been described (see scheme). In a single palladium-catalyzed reaction the catalyst mediates two consecutive carbonylation steps, thereby converting five components (aryl iodide, two units imine, and two units CO) into an imidazoline ring.

A highly diastereoselective synthesis of α-hydroxy-β-amino acid derivatives via a Lewis acid catalyzed three-component condensation reaction

A very efficient three-component synthesis of a series of syn α-hydroxy-β-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.

Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation Protocol for the synthesis of indenoisoquinolines

Copper-catalyzed coupling of imines, vinylstannanes, or alkynes and o-bromoaroyl chlorides followed by Pd(0)-catalyzed annulations afforded indenoisoquinolines. Protocols requiring minimal purifications were developed, providing new methods for the construction of combinatorial libraries.

Eco-friendly synthesis of imines by ultrasound irradiation

A series of imines was synthesized by an ultrasound-assisted reaction of aldehydes and primary amines using silica as the promoter. Products were obtained in high yields even in large scale synthesis.

Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: Efficient and diastereoselective synthesis of multisubstituted pyrrolidines

A tandem ring-opening-cyclization reaction of cyclopropanes with imines in the presence of 5 mol% of scandium triflate was developed for the highly diastereoselective synthesis of multisubstituted pyrrolidines. The Royal Society of Chemistry 2006.