119924-24-2Relevant academic research and scientific papers
Rh(III)-catalyzed halogenation of vinylic C-H bonds: Rapid and general access to Z-halo acrylamides
Kuhl, Nadine,Schroeder, Nils,Glorius, Frank
, p. 3860 - 3863 (2013)
Herein, the regio- and stereoselective iodination, along with some examples for the bromination, of readily available acrylamides to access a variety of differently substituted Z-haloacrylic acid derivatives is reported. The reaction proceeds under mild conditions via a Rh(III)-catalyzed C-H-activation/ halogenation mechanism and represents a rare example of a direct halogenation of electron-poor acrylic acid derivatives.
Synthesis and in vitro antitrypanosomal activity of novel Nifurtimox analogues
Pozas, Rocio,Carballo, Javier,Castro, Clementina,Rubio, Julieta
, p. 1417 - 1421 (2005)
Eight novel analogues of Nifurtimox, 4-[(5-nitrofurfurylidene)amino]-3- methylthiomorpholine-1,1-dioxide, containing alfa-beta unsaturated amides, were synthesized and evaluated for their in vitro activity against Trypanosoma cruzi epimastigotes. Four der
Substituted Tetraethynylethylene–Tetravinylethylene Hybrids
Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin
supporting information, p. 977 - 986 (2022/02/03)
A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w
Multicomponent Enantioselective Synthesis of Tetrahydropyridazinones Employing Chiral α,β-Unsaturated Acylammonium Salts
Kiledal, Sigrid A.,Jourdain, Roxane,Vellalath, Sreekumar,Romo, Daniel
supporting information, p. 6622 - 6627 (2021/09/13)
An enantioselective three-component reaction was developed for the synthesis of tetrahydropyridazinones employing chiral α,β-unsaturated acylammonium salts, malonates, and azodicarboxylates. An initial α-amination of a malonate with an azodicarboxylate an
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
Practical access to fluorescent 2,3-naphthalimide derivatives: Via didehydro-Diels-Alder reaction
Chen, Xia,Zhong, Cheng,Lu, Yuling,Yao, Meng,Guan, Zhenhua,Chen, Chunmei,Zhu, Hucheng,Luo, Zengwei,Zhang, Yonghui
supporting information, p. 5155 - 5158 (2021/05/31)
A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.
Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes
Lee, Yong Ho,Denton, Elliott H.,Morandi, Bill
supporting information, p. 20948 - 20955 (2020/12/21)
We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.
Organic metal compound and organic light-emitting device
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Paragraph 0041; 0061, (2020/02/10)
Organic metal compounds and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II): In particular, one of the following two conditions (1) and (2) is met: (1) R1 is deuterium or C1-6 deuterated alkyl group, when R3 and R4 are independently hydrogen, halogen, C1-6 alkyl group, C1-6 fluoroalkyl or C3-12 heteroaryl group; and (2) R1 is hydrogen, deuterium, C1-6 alkyl group, C1-6 deuterated alkyl group, C3-12 heteroaryl group, or C6-12 aryl group, when at least one of R3 and R4 is C6-12 aryl group or C6-12 fluoroaryl group.
Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
, p. 2590 - 2602 (2020/11/18)
A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
Visible Light-Mediated Synthesis of Enantiopure γ-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids
Kerres, Sabine,Plut, Eva,Malcherek, Simon,Rehbein, Julia,Reiser, Oliver
supporting information, (2019/02/07)
A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-azabicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobutane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant, is described.
