16205-99-5Relevant academic research and scientific papers
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Borane-Catalyzed Reductive α-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact
Kim, Youngchan,Chang, Sukbok
supporting information, p. 218 - 222 (2016/01/25)
Described herein is the development of the B(C6F5)3-catalyzed hydrosilylation of α,β-unsaturated esters and amides to afford synthetically valuable α-silyl carbonyl products. The α-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate.
Antileishmanial lead structures from nature: Analysis of structure-activity relationships of a compound library derived from caffeic acid bornyl ester
Glaser, Jan,Schultheis, Martina,Hazra, Sudipta,Hazra, Banasri,Moll, Heidrun,Schurigt, Uta,Holzgrabe, Ulrike
, p. 1394 - 1410 (2014/03/21)
Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 μM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.
Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives
Singh, Manjeet,Kumar, Sunil,Kumar, Ashwani,Kumar, Pradeep,Narasimhan, Balasubramanian
experimental part, p. 511 - 522 (2012/08/07)
A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.
Synthesis of chiral 2-arylpropenoic esters by the palladium catalyzed carbonylation of arylacetylenes
Monteiro, Adriano L.,Lando, Vanusa R.,Gasparini, Vanessa
, p. 3605 - 3611 (2007/10/03)
A simple method is described for the synthesis of chiral 2-arylpropenoic esters by carbonylation of arylacetylenes in the presence of chiral alcohols catalyzed by palladium complexes under mild conditions (10 atm, 100°C, 2h) with high yields.
REACTION OF BENZYLIDENEBENZYLAMINE WITH CINNAMIC ACID DERIVATIVES UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS. I. SYNTHESIS OF β-ARYL-γ-PHENYL-γ-AMINOBUTYRIC ACIDS AND THEIR DERIVATIVES
Potapov, V. M.,Gracheva, R. A.,Sivov, N. A.,Savina, S. A.,Sivova, L. A.
, p. 1694 - 1699 (2007/10/02)
The reaction of benzylidenebenzylamine with the esters of substituted cinnamic acids under the conditions of phase-transfer catalysis gives high yields of β-aryl-γ-phenyl-γ-aminobutyric acids and their derivatives (hydrochlorides, 4-aryl-5-phenyl-2-pyrrolidones).
Reaction of Grignard Reagents with Benzaldehyde, 2,2-Dimethylpropanal and Cinnamates of Chiral Alcohols in Chiral Solvents
Jalander, Lars,Strandberg, Rolf
, p. 15 - 20 (2007/10/02)
The asymmetric induction in a Grignard reaction carried out in (-)-1-isopropyl-2-methoxy-4-methylcyclohexane was higher than in the reaction carried out in (+)-1-methoxy-2-methylbutane.The chirality of the solvent contributed more than that of the reagent stereodifferentiation in the reaction of (+)-2-methylbutylmagnesium bromide with benzaldehyde in (+)-1-methoxy-2-methylbutane.
