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Relevant academic research and scientific papers

Switchable perfomance of an L-proline-derived basic catalyst controlled by supramolecular gelation

An L-proline-derived low molecular weight gelator forms gels in nitromethane and nitroethane and acts as a basic catalyst for the Henry nitroaldol reaction of these solvents with 4-nitrobenzaldehyde and 4-chlorobenzaldehyde. The reported catalyst is effic

Use of protease from Bacillus licheniformis as promiscuous catalyst for organic synthesis: Applications in C-C and C-N bond formation reactions

Commercially available protease from Bacillus licheniformis has been used in different non-conventional biotransformations showing remarkable activity values. The promiscuous behaviour of this enzyme used in the cross-linked enzyme aggregates immobilized form (Alcalase-CLEA), has been successfully demonstrated for the first time in C-C bond formation processes such as aldol, Henry and Mannich reactions. On the other hand, the Bayllis-Hillman reaction between 4-nitrobenzaldehyde and methyl vinyl ketone occurred through unspecific catalysis. Interestingly, aza- Michael addition reactions of secondary amines (diethylamine, piperidine and pyrrolidine) to acrylonitrile have been also efficiently catalyzed, observing with diethylamine the most remarkable differences between the enzyme-mediated reaction and the one in the absence of catalyst. Higher reactivities were attained with pyrrolidine demonstrating the versatility of hydrolases in organic synthesis. Copyright

Reaction-dependent heteroatom modification of acid-base catalytic cooperativity in aminosilica materials

The effects of heteroatom substitution on the cooperative catalytic activity of a series of bifunctional acid-base aminosilica catalysts are probed in aldol and nitroaldol condensations. Three M3+ (B, Al, and Ga) and three M4+ (Ti, Zr, and Ce) heteroatoms are incorporated into different samples of SBA-15 silica and then grafted with aminosilanes to produce bifunctional acid-base catalysts. The catalytic activity of each material is measured in the aldol condensation of 4-nitrobenzaldehyde with acetone at 50 °C and the nitroaldol condensation of 4-nitrobenzaldehyde with nitromethane at 40 °C and compared to the catalytic activity of a heteroatom-free aminosilica catalyst. The heteroatom substitutions produce catalysts with larger amounts of strong Lewis acid sites compared to the heteroatom-free aminosilica catalyst. We rationalize these results in the context of the physical (e.g. surface area, pore diameter, particle size) and chemical properties (e.g. total number and strength of acid sites) of each material and the proposed catalytic mechanisms of the two reactions. The increase in the number of strong Lewis acid sites of each heteroatom material decreased its activity in the aldol condensation, though four heteroatom substitutions (B, Al, Ga, and Ti) increased the catalytic activity of the aminosilica catalyst in the nitroaldol condensation. The results suggest that inclusion of a small amount of Lewis acid sites in aminosilica materials can increase the cooperative catalytic activity of the materials in the nitroaldol condensation. The results also suggest that inclusion of Lewis acid sites in aminosilica materials decreases the cooperative catalytic activity of the materials in the aldol condensation.

Continuous Henry reaction to a specific product over nanoporous silica-supported amine catalysts on fixed bed reactor

We report a method for continuously producing the nitroaldol, the nitrostyrene, or the Michael product by performing the Henry reaction over a fixed bed reactor that is packed with primary or secondary amine-functionalized nanoporous materials. The % conv

Supramolecular catalysis with extended aggregates and gels: Inversion of stereoselectivity caused by self-assembly

L-Proline-L-valine dipeptide derivatives, which self-assemble in toluene, have been studied as stereoselective catalysts in the conjugate addition of cyclohexanone to trans-β-nitrostyrene. Remarkable effects on the stereoselectivity are observed associated to the aggregation of the catalyst. Outstanding differences were observed between the catalytic activity of compound 1, which forms supramolecular gels in toluene, and compound 2, which is not a gelator. In the former case, the enantioselectivity of the reaction was almost insensitive to changes in catalyst concentration and temperature, but in the case of compound 2, the catalytic activity was very much affected by those variables. Structural studies indicate that the results can be rationalized by taking into account significant conformational changes experienced by the catalytic L-proline derivatives associated with the aggregation process. The results highlight that catalyst selfassembly is a very important issue to consider in the stereoselective outcome of organocatalytic reactions. Especially relevant is the fact that the use of supramolecular gels as organocatalyts emerges as a technique that affords reliable and constant stereoselectivity in different conditions with the added value of easy catalyst recovery.

Co-Polymeric Nanosponges from Cellulose Biomass as Heterogeneous Catalysts for amine-catalyzed Organic Reactions

Heterogeneous catalysts prepared from biomass waste sources are attracting increasing interest. The reasons rely on the possibility of combining the virtuous approach of circular economy with the consolidated advantages of heterogeneous catalysis, namely the recycling of the system and the possibility to drive selectivity towards desired products. Herein we report a highly porous cellulose-based nanosponge (CNS) and its use as a recoverable catalyst for Henry and Knoevenagel reactions, two classical amino-catalyzed transformations. The material is obtained by cross-linking between TEMPO-oxidized cellulose nanofibers (TOCNF) and branched polyethyleneimine 25 kDa (bPEI) in the presence of citric acid. CNS have been developed as sorbent materials for water remediation but their use as heterogeneous catalysts was never investigated. The fully characterized micro- and nano-porous system guarantees a complete penetration of CNS, allowing reagents to diffuse within. Indeed, by modulating reaction conditions (catalyst loading, temperature, solvent, microwave versus conventional heating, relative ratio of reagents) it was possible to drive selectivity towards the desired products, while maintaining high efficiency in terms of conversion. The catalyst could be re-used several times without losing in catalytic efficiency. In most cases the products’ distribution is quite different from homogeneous conditions, this much more emphasizing the importance of this heterogeneous solution.

Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15

The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding aldehydes with CH3NO2 catalyzed by n-C6H13NH2.

KINASE INHIBITORS

The present invention relates to compounds of Formula I or a pharmaceutically acceptable salt thereof, wherein variables R, Ar, X, and Ar1 and n are as defined herein. The compounds are capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

Protein-mediated nitroaldol addition in aqueous media. Catalytic promiscuity or unspecific catalysis?

A high efficient and environmentally friendly procedure for the production of aromatic and heteroaromatic β-nitroalcohols has been developed. This synthetic approach involves the condensation of an appropriate aldehyde with 1-nitroalkanes in aqueous media

Cooperative catalysis of primary and tertiary amines immobilized on oxide surfaces for one-pot C-C bond forming reactions

(Chemical Equation Presented) D'you know what amine? Primary and tertiary amines are both immobilized on the same silica-alumina surface by silane-coupling reactions. The resultant silica-alumina-supported double-amines are found to exhibit excellent catalysis for 1,3-dinitroalkane synthesis from various aldehydes with nitromethane. A cooperative catalytic mechanism on the solid surface for this efficient synthesis is proposed.