5660-83-3Relevant academic research and scientific papers
Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds
Wu, Hui-Chun,Wang, Chen,Chen, Ying-Han,Liu, Yan-Kai
supporting information, p. 1762 - 1765 (2021/02/27)
An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.
ACETAMIDO DERIVATIVES AS DNA POLYMERASE THETA INHIBITORS
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Paragraph 0196, (2020/08/22)
Disclosed herein are certain acetamido derivatives that are DNA Polymerase Theta (Polθ) inhibitors of Formula (I). Also, disclosed are pharmaceutical compositions comprising such compounds and methods of treating diseases treatable by inhibition of Polθ such as cancer, including homologous recombination (HR) deficient cancers.
Method used for preparing substituted 1, 3-malononitrile
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Paragraph 0042-0043, (2019/08/07)
The invention belongs to the field of fine chemical product preparation and medicine intermediate synthesis, and relates to a method used for preparing substituted 1, 3-malononitrile. According to themethod, an aldehyde or a ketone and malononitrile are subjected to condensation reaction to prepare substituted 1, 3-malononitrile, wherein water is taken as a solvent, the aldehyde or the ketone andmalononitrile are subjected to Knoevenagel condensation under catalytic effect of zinc proline so as to obtain the corresponding substituted 1, 3-malononitrile. The method conditions are mild; operation is convenient; water is taken as a reaction solvent, so that the method is friendly to the environment; and the application prospect is promising.
Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity
Martelli, Lorena S.R.,Vieira, Lucas C.C.,Paix?o, Márcio W.,Zukerman-Schpector, Julio,de Souza, Juliana O.,Aguiar, Anna Caroline C.,Oliva, Glaucius,Guido, Rafael V.C.,Corrêa, Arlene G.
supporting information, p. 3530 - 3542 (2019/05/24)
The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.
Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature
Burate, Pralhad A.,Javle, Balasaheb R.,Desale, Pranjal H.,Kinage, Anil K.
, p. 2368 - 2375 (2019/06/17)
Abstract: Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with malononitrile and ethyl cyanoacetate. The reaction proceeds at room temperature without using any organic solvent and is very fast with good to excellent yield. Additionally, the catalyst is easily separable and recyclable without loss of activity. Graphic Abstract: [Figure not available: see fulltext.].
Cross-Linked Polyamine from Imidazolium-Based Materials: A Simple Route to Useful Catalytic Materials
Campisciano, Vincenzo,Salvo, Anna Maria Pia,Liotta, Leonarda Francesca,Spinella, Alberto,Giacalone, Francesco,Gruttadauria, Michelangelo
, p. 1352 - 1358 (2018/04/02)
Cross-linked polyamine-based materials were easily prepared by reduction of the corresponding cross-linked imidazolium-based materials with sodium borohydride in hot ethanol. Overall, the synthetic procedure is based on the polymerization of a suitable bis-vinylimidazolium salt with or without a suitable support, such as silica or silica-coated magnetic nanoparticles (γ-Fe2O3@SiO2), followed by reduction. This simple approach allows the synthesis of materials based on a network of secondary and tertiary amines. Materials were characterized by 13C cross-polarization magic angle spinning NMR (13C CPMAS NMR), proton spin-lattice relaxation times in the rotating frame (T1ρH) and thermogravimetric analysis (TGA). Cross-linked polyamine-based materials were used as recoverable catalyst for Knoevenagel reaction. High yields of the condensation products were obtained and up to 11 cycles were carried out.
Polyoxoniobates as a superior Lewis base efficiently catalyzed Knoevenagel condensation
Xu, Qiaofei,Niu, Yanjun,Wang, Guan,Li, Yingguang,Zhao, Yuan,Singh, Vikram,Niu, Jingyang,Wang, Jingping
, p. 93 - 99 (2018/05/22)
The outstanding basicity of negative charged Lindqvist type Polyoxoniobate K7HNb6O19·13H2O (Nb6) have been proved experimentally as well as by theoretical NBO calculations, the results insights high electron density on terminal and bridging oxygen atoms of niobate anion. The most negative Natural Bond Orbital charge (NBO) of oxygen in Nb6 is ?1.001, which is a much more negative value than those reported in other polyoxometalates, that corroborates its high basicity thus likely to be employed as a strong base catalyst. Experimental study suggests that Nb6 can efficiently catalyze Knoevenagel condensation of various carbonyl compounds with active methylene compounds neglecting the steric and electronic effect of aromatic aldehydes under mild conditions. Kinetic test shows that Knoevenagel condensation of benzaldehyde with ethyl cyanoacetate exhibits second-order kinetics in the presence of Nb6 and the calculated activation energy is 43.3 kJ mol?1. Meanwhile, a proper mechanism according to the NBO study speculates that the most negative charged terminal oxygens in Nb6 would be pivotal in this transformation.
THIENOPYRIDINE CARBOXAMIDES AS UBIQUITIN-SPECIFIC PROTEASE INHIBITORS
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Paragraph 00283, (2017/09/05)
The disclosure relates to inhibitors of USP28 and/or USP25 useful in the treatment of cancers, inflammation, autoimmune diseases, and infectious diseases, having the Formula (I), where R1, R2, R3, R4, R5, R5', R6, R7, X, m, and n are described herein.
Assembly of Terpenoid Cores by a Simple, Tunable Strategy
Lahtigui, Ouidad,Emmetiere, Fabien,Zhang, Wei,Jirmo, Liban,Toledo-Roy, Samira,Hershberger, John C.,Macho, Jocelyn M.,Grenning, Alexander J.
supporting information, p. 15792 - 15796 (2016/12/16)
Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
Interplay between hydrophobicity and basicity toward the catalytic activity of isoreticular MOF organocatalysts
Abedi, Sedigheh,Azhdari Tehrani, Alireza,Ghasempour, Hosein,Morsali, Ali
, p. 6970 - 6976 (2016/08/09)
Due to the structural diversity of metal-organic frameworks, MOFs, tailored engineering of these compounds is important for their use in catalytic processes. Among the MOFs tested as heterogeneous catalysts, there have been rare reports of size selective catalysts. In the present work, we could successfully indicate that subtle substrate selectivity can be induced in the catalytic system by designing a series of isoreticular MOFs with slight structural modifications. Four MOF catalysts possessing imine and/or amine basic N-donor pillars bearing phenyl or naphtyl cores showing different hydrophobic characters around the basic reaction center were prepared via a simple mechano-chemical synthesis. They were characterized thoroughly using TG, IR and PXRD analysis. For the first time, the aldol-type condensation reaction of malononitrile with ketone-functionalized carbonyl substrates was developed in the presence of the basic MOF organocatalysts. Moreover, it has been successfully shown that a subtle substrate selectivity can be addressed during the reaction of three slightly different α,β-unsaturated carbonyl compounds in contrast to the effect of size control barriers that commonly direct a heterogeneous reaction pathway.
