- Chemoselective Transfer Hydrogenation of Enamides Using Ru Pincer Complexes for the Synthesis of α-Amino Acids
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The chemoselective reduction of enamides to α-amino acids with iPrOH and EtOH as H-donors and solvents catalyzed by Ru pincer complexes is demonstrated. A range of α-amino acids is synthesized in good to excellent yields. Applications, large scale, and a one-pot experiment are also reported. Finally, deuterium-labeling experiments show high regioselectivity between the α-and β-positions of the alkene unit.
- Pinheiro, Danielle L. J.,Nielsen, Martin
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p. 5419 - 5423
(2022/03/14)
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- Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
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An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
- Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
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- Enantioselective [4 + 2]-Annulation of Azlactones with Copper-Allenylidenes under Cooperative Catalysis: Synthesis of α-Quaternary α-Acylaminoamides
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The first enantioselective decarboxylative [4 + 2]-annulation of ethynyl benzoxazinanones with azlactones has been developed under cooperative copper and bifunctional tertiary aminourea catalysis. This direct and modular approach combines dipolar copper-a
- Simlandy, Amit Kumar,Ghosh, Biki,Mukherjee, Santanu
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supporting information
(2019/05/08)
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- An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions
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An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.
- Jagadale, Megha,Naikwade, Altafhusen,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 10993 - 11005
(2018/07/06)
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- Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
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A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
- Liu, Xuan-Qi,Liu, Ya-Qin,Shao, Xu-Sheng,Xu, Zhi-Ping,Xu, Xiao-Yong,Li, Zhong
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- Synthesis and quantitative structure-activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
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A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure eactivity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (Sθ) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.
- Yang, Jing,Ma, Min,Wang, Xue-Ding,Jiang, Xing-Jun,Zhang, Yuan-Yuan,Yang, Wei-Qing,Li, Zi-Cheng,Wang, Xi-Hong,Yang, Bin,Ma, Meng-Lin
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- Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
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Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t)ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 μM in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors.
- Wang, Peiyuan,Naduthambi, Devan,Mosley, Ralph T.,Niu, Congrong,Furman, Phillip A.,Otto, Michael J.,Sofia, Michael J.
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scheme or table
p. 4642 - 4647
(2011/09/12)
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- A simple and efficient method for the synthesis of Erlenmeyer azlactones
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We have recently developed a novel and efficient method for synthesising Erlenmeyer azlactones under mild and rapid conditions. The reaction is performed by reacting 2-phenyl-5-oxazolone with an aldehyde in dichloromethane using alumina as a catalyst. The materials react instantly at room temperature, negating the need for high temperatures and long reaction times. We have successfully used this method for both aliphatic, aromatic and heteroaromatic aldehydes, synthesising previously unmade Erlenmeyer azlactones in moderate to high yields.
- Conway, Philip A.,Devine, Kevin,Paradisi, Francesca
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experimental part
p. 2935 - 2938
(2009/05/30)
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- Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters
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The alkyl, aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in me
- Maekawa, Kei,Hishikawa, Norikazu,Kubo, Kanji,Igarashi, Tetsutaro,Sakurai, Tadamitsu
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p. 11267 - 11281
(2008/03/12)
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- Study on dry-media microwave azalactone synthesis on different supported KF catalysts: Influence of textural and acid-base properties of supports
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Twenty-five inorganic solids studied as supports for KF were screened with respect to the synthesis of the azalactone obtained by dry-media condensation of p-hydroxybenzaldehyde with hippuric acid in acetic anhydride (1:1:4, molar ratio), in 3 g of 10 wt%
- Bautista, Felipa M.,Campelo, Juan M.,Garcia, Angel,Luna, Diego,Marinas, Jose M.,Romero, Antonio A.
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p. 227 - 234
(2007/10/03)
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- Phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
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A non-nucleoside class of compounds that inhibits the replication of hepatitis B virus (HBV) in cell culture has been discovered. A series of substituted analogues of phenylpropenamide 6 has been prepared and evaluated in the HepAD38 cellular assay. Structure-activity relationships of this series are discussed. (C) 2000 Elsevier Science Ltd.
- Perni, Robert B.,Conway, Samuel C.,Ladner, Stephanie K.,Zaifert, Katie,Otto, Michael J.,King, Robert W.
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p. 2687 - 2690
(2007/10/03)
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- Synthesis of Isomeric Methyl- and Dimethyl-Substituted 4-Benzylidene-2-phenyloxazolin-5-ones and Ring-Opened Derivatives
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4-Benzylidene-2-phenyloxazolin-5-one and 15 mono- and dimethylated isomers as well as their ring-opened methyl ester and acid derivatives have been synthesized.Absorption spectroscopy indicates insignificant changes in the chromophore due to the methyl groups.
- Nicholas, Everton S.,Phelps, David J.
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