3464-18-4Relevant academic research and scientific papers
Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α,β-unsaturated amides
Huang, Zijun,Jiang, Xiongwei,Lan, Donghui,Li, Yuehui,Pi, Shaofeng,Tan, Zhengde,Tang, Jia,Xie, Tianle,Yi, Bing,Zhang, Minmin
supporting information, (2022/02/22)
α,β-Unsaturated primary amides are important intermediates and building blocks in organic synthesis. Herein, we report a ligand-free iron-catalyzed hydroaminocarbonylation of alkynes using NH4HCO3 as the ammonia source, enabling the highly efficient and regioselective synthesis of linear α,β-unsaturated primary amides. Various aromatic and aliphatic alkynes are transformed into the desired linear α,β-unsaturated primary amides in good to excellent yields. Further studies show that using NH4HCO3 as the ammonia source is key to obtain good yields and selectivity. The utility of this route is demonstrated with the synthesis of linear α,β-unsaturated amides including vanilloid receptor-1 antagonist TRPV-1.
Stereoselective One-Pot Synthesis of cis-1,2-Dicyanoalkenes from 1,1-Bis(benzenesulfonyl)alkenes and KCN
Zhang, Yue,Wei, Yi,Li, Shen,Ma, Jun-An
, p. 199 - 203 (2019/01/04)
An efficient synthesis of cis-1,2-dicyanoalkenes by the reaction of 1,1-bis(benzenesulfonyl)alkenes with KCN was developed. This reaction was conducted in the presence of tetrabutylammonium bromide and NH4Cl/K3PO4 under phase-transfer conditions. A series of cis-1,2-dicyanoalkenes were obtained in good to high yields. Further transformation of the obtained product allows for access to imide and dicarboxylic acid compounds.
Mild Decarboxylative C?H Alkylation: Computational Insights for Solvent-Robust Ruthenium(II) Domino Manifold
Kumar, N. Y. Phani,Rogge, Torben,Yetra, Santhivardhana Reddy,Bechtoldt, Alexander,Clot, Eric,Ackermann, Lutz
supporting information, p. 17449 - 17453 (2017/10/23)
Computational studies on decarboxylative C?H alkenylations provided key insights into the solvent-robust nature of C?H activation/decarboxylation domino reactions. These properties were exploited for ruthenium(II)-catalyzed C?H alkylations by a decarboxylative process with ample scope under copper-free and silver-free reaction conditions.
Selective and tunable synthesis of 3-arylsuccinimides and 3-arylmaleimides from arenediazonium tetrafluoroborates and maleimides
Yang, Zhen-Hua,Chen, Zhong-Hui,An, Yu-Long,Zhao, Sheng-Yin
, p. 23438 - 23447 (2016/03/12)
A highly efficient synthetic strategy for synthesizing 3-arylsuccinimides has been developed from arenediazonium tetrafluoroborates and maleimides in the presence of TiCl3. The reactions generated 3-arylsuccinimides in satisfactory yields under mild reaction conditions. In addition, 3-arylmaleimides were obtained by the coupling of arenediazonium tetrafluoroborate and maleimides catalyzed by CuCl. This methodology provided the selective and tunable synthesis of two classes of products by simply switching different metal reagents. The methods are simple, efficient and practical.
Synthetic derivatives of isoquinoline, dicarboxylic acid imides and thioimides as bioactive compounds
Solecka, Jolanta,Rajnisz, Aleksandra,Postek, Magdalena,Laudy, Agnieszka E.,Szawka?o, Joanna,Czarnocki, Zbigniew
, p. 1181 - 1189 (2016/10/17)
This study is a continuation of a research program aimed at identifying potent drugs against bacterial infections, in which a series of organic compounds: dicarboxylic acid imides and thioimides, isoquinoline derivatives and open chain compounds, were examined for antimicrobial properties against Staphylococcus aureus and Escherichia coli. In effect of this investigation, the most active compounds (35-40, 47) were selected for in vitro tests against fourteen clinically important pathogenic isolates, the methicillin resistant Staphylococcus aureus (MRSA) and several reference Gram-negative bacteria: Proteus vulgaris, Pseudomonas aeruginosa, Klebsiella pneumonia, Stenotrophomonas maltophilia, and Acinetobacter baumannii. The obtained data revealed that seven compounds (three dithioimides, 35, 39, 47, and four thioimides, 36-38, 40) exhibit effective antibacterial activity against the tested Staphylococcus aureus MSSA and MRSA strains. Among them, dicarboxylic acid thioimides 37 and 38 were proven to be the most active.
Design, synthesis and anticonvulsant properties of new N-Mannich bases derived from 3-phenylpyrrolidine-2,5-diones
Kamiński, Krzysztof,Obniska, Jolanta,Chlebek, Iwona,Wiklik, Beata,Rzepka, Sabina
, p. 6821 - 6830 (2013/10/22)
The synthesis and anticonvulsant properties of new N-Mannich bases of 3-phenyl- (9a-d), 3-(2-chlorophenyl)- (10a-d), 3-(3-chlorophenyl)- (11a-d) and 3-(4-chlorophenyl)-pyrrolidine-2,5-diones (12a-d) were described. The key synthetic strategies involve the
Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues
Berhal, Farouk,Wu, Zi,Genet, Jean-Pierre,Ayad, Tahar,Ratovelomanana-Vidal, Virginie
scheme or table, p. 6320 - 6326 (2011/10/05)
Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogues in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF3-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biological interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization.
Synthesis, physicochemical and anticonvulsant properties of new N-[(4-arylpiperazin-1-yl)alkyl]-3-phenyl- and 3-(3-methyl-phenyl)-pyrrolidine-2, 5-diones
Obniska, Jolanta,Chlebek, Iwona,Pichor, Joanna,Kopytko, Maciej,Kaminski, Krzysztof
experimental part, p. 639 - 647 (2010/08/05)
The series of N-[(4-arylpiperazin-1-yl)-alkyl]-3-phenyl- and 3-(3-methylphenyl)-pyrrolidine-2,5-diones [VIII-XXV] were synthesized and evaluated for anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed in mice, using in
Microwave-enhanced rhodium-catalyzed conjugate-addition of aryl boronic acids to unprotected maleimides
Iyer, Pravin S.,O'Malley, Meaghan M.,Lucas, Matthew C.
, p. 4413 - 4418 (2008/02/03)
Various boronic acids were treated with a rhodium (I) catalyst enabling their 1,4-conjugate addition to unprotected maleimide. The scope of the reaction was explored to include both electron-rich and electron poor boronic acids. These reactions were also
