- Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex
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Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.
- Kimaru, Natsuki,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru
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supporting information
p. 6133 - 6136
(2021/06/30)
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- RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate
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A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.
- Das, Debapratim,Sahoo, Gopal,Biswas, Aniruddha,Samanta, Rajarshi
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supporting information
p. 360 - 364
(2020/01/25)
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- Phytotoxicity, structural and computational analysis of 2-methyl-1,5-diarylpentadienones
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In our studies aimed to produce new chemicals used in weed control, 2-methyl-1,5-diarylpentadienones were synthesized by the reaction of p-methoxybenzaldehyde, p-nitrobenzaldehyde and p-N,N-dimethylbenzaldehyde, respectively, with 2-butanone, resulting in four model compounds. The phytotoxicity of these compounds against wheat coleoptiles and Sesame seedling was observed at μM concentrations, indicating good potential for their usage in weed management in the field. Spectroscopic and computational studies were performed in order to gain understanding on their mechanisms of action and to clarify some structural complexities due existence of conformers and substituent effects. These compounds probably act as hydroxyphenylpyruvate dioxygenase inhibitors. The tested compounds were characterized by spectroscopic and single crystal X-ray diffraction analyses. Solid crystalline state of the compound A (2-Methyl-1-(p-methophyphenyl)-5-(phenyl)-diarylpentadienone) is observed in the monoclinic space group P21/c with unit cell dimensions a = 14.3366(4) ?, b = 11.3788(4) ?, c = 9.6319(3) ?, β = 96.596, V = 1560.88(9) ?3 and Z = 4. Compound C (2-Methyl-1-(p-methophyphenyl)-5-(p-nitrophenyl)-diarylpentadienone) crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 17.8276(9) ?, b = 7.3627(4) ?, c = 12.9740(6) ?, β = 107.6230(10), V = 1623.04(14) ?3 and Z = 4. LC-UV-MS analysis furnished important data helpful for their characterization. The spectroscopic data and computational (DFT) analysis revealed the fact that each of the compounds A-D occurs in solution as four conformers.
- Din, Zia Ud,Rodrigues-Filho, Edson,de Cassia Pereira, Viviane,Gualtieri, Sonia Cristina Juliano,Deflon, Victor Marcelo,da Silva Maia, Pedro Ivo,Kuznetsov, Aleksey E.
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p. 239 - 247
(2017/04/26)
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- Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids
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In this work the screening of 20 unsymmetrical chalcone and curcuminoids analogues in regard of their antimicrobial properties was conducted. Electron donating groups in the aromatic rings in the chalcone and curcuminoid derivatives produced higher antimicrobial effect. Compounds 1, 9 and 15 exhibited good activity against Escherichia coli and Staphylococcus aureus. These compounds were further evaluated against nine micro-organisms of pathological interest. Pharmmaper was used for target fishing of compounds against important bacterial targets. Molecular Docking helped to verify the results of these compounds against the selected bacterial target D-alanyl-D-alanine carboxypeptidase (PDB ID: 1PW1). The crystal structure of ligand and docked conformers in the active site of 1PW1 were analyzed. As a result structure-activity relationships are proposed. Structures of compounds 14 and 16 were obtained through single crystals X-ray diffraction studies. Compound 14 crystallizes in monoclinic space group P21/c with unit cell dimensions a = 13.1293(3) ?, b = 17.5364(4) ?, c = 15.1433(3) ?, β = 95.6440(10), V = 3469.70(13) ?3 and Z = 8. Compound 16 crystallizes in triclinic space group Pī with unit cell dimensions a = 6.8226(4) ?, b = 7.2256(4) ?, c = 18.1235(12) ?, β = 87.322(4), V = 850.57(9) ?3 and Z = 2.
- Ud Din, Zia,Serrano,Ademi, Kastriot,Sousa,Deflon, Victor Marcelo,Maia, Pedro Ivo da Silva,Rodrigues-Filho, Edson
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p. 529 - 534
(2017/05/26)
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- Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
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Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten- 2-one (R = n-pentyl, phenyl, 2′- and 4′-chlorophenyl, 3′- and 4′-nitrophenyl, 4′-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae andGeotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones.
- De Paula, Bruno R.S.,Zampieri, Davila S.,Rodrigues, J. Augusto R.,Moran, Paulo J.S.
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p. 973 - 981
(2013/09/23)
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- RuCl3 catalyses aldol condensations of aldehydes and ketones
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Anhydrous RuCl3 catalyses the efficient cross aldol condensations of different ketones with various aromatic aldehydes in sealed tube under solvent free conditions without the occurrence of any self condensations. Regioselective self condensation reaction of some ketones and aldehydes are also described. The catalytic effect of Ru(III) is shown by performing similar reactions under thermal conditions without catalyst.
- Iranpoor, Nasser,Kazemi, Foad
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p. 9475 - 9480
(2007/10/03)
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