61275-22-7Relevant articles and documents
INHIBITORS OF RAF KINASES
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Paragraph 00852; 00855-00856, (2021/04/30)
Provided herein are inhibitors of receptor tyrosine kinase effector, RAF, pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.
Straightforward Synthesis of Fluorinated Enals via Photocatalytic α-Perfluoroalkenylation of Aldehydes
Wulkesch, Christian,Czekelius, Constantin
, p. 7425 - 7438 (2021/06/21)
(Per)fluorinated substances represent an important compound class with regard to drug design and material chemistry. We found a mild, operationally simple, and inexpensive photocatalytic perfluoroalkenylation reaction giving tetrasubstituted, highly electron-deficient enals straight from aldehydes. This one-step reaction tolerates various functional groups and can be applied to a wide range of substrates giving the products in yields of 52-84%.
Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates
Ponath, Sebastian,Menger, Martina,Grothues, Lydia,Weber, Manuela,Lentz, Dieter,Strohmann, Carsten,Christmann, Mathias
supporting information, p. 11683 - 11687 (2018/09/10)
Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.
Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts
Mao, Hui,Kim, Dong Wan,Shin, Hun Yi,Song, Choong Eui,Yang, Jung Woon
supporting information, p. 1355 - 1362 (2017/02/15)
The regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives was achieved through transition-metal-free, reductive cyclisation of ortho-formyl trans-cinnamaldehydes with Hantzsch ester in the presence of an aminocatalyst. In particular, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.
Preparation of the MacMillan imidazolidinones
Samulis, Leopold,Tomkinson, Nicholas C.O.
experimental part, p. 4263 - 4267 (2011/06/26)
A general method for the preparation of the MacMillan imidazolidinones is described. Treatment of an α-amino amide with a carbonyl compound in refluxing chloroform in the presence of Yb(OTf)3 (1 mol %) provides convenient access to the corresponding imidazolidinones.
Highly efficient stereoconservative amidation and deamidation of α-amino acids
Shendage, Deepak M.,Froehlich, Roland,Haufe, Guenter
, p. 3675 - 3678 (2007/10/03)
(Chemical Equation Presented) An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N-alkyl secondary amides of α-amino acids can be generated from corresponding N-phthaloyl amino acids by coupling reaction of N-alkylamines using mixed anhydride method. These secondary amides can be transformed by thermal rearrangement of intermediate nitrosoamides to O-alkyl esters with retention of configuration and excellent yields.
Structural and thermodynamic characterization of temperature-dependent changes in the folding pattern of a synthetic triamide
Dado, Gregory P.,Gellman, Samuel H.
, p. 4228 - 4245 (2007/10/02)
Variable-temperature 1H NMR and IR studies of triamide 1 and related compounds indicate that 1 undergoes dramatic temperature-dependent conformational changes in relatively nonpolar solvents (methylene chloride and chloroform). The folding pattern favored at low temperatures in these chlorocarbons (1c) contains a single C=O?H-N hydrogen bond in a nine-membered ring, while a folding pattern containing only a six-membered-ring C=O?N-H interaction (1a) is favored at higher temperatures. Dimethyl sulfoxide, a very strong hydrogen-bond-accepting solvent, disrupts all internal hydrogen bonding in 1. Acetonitrile appears to disrupt the six-membered-ring hydrogen bond selectively and to promote nine-membered-ring interaction at room temperature, relative to chlorocarbon solvents. By treating the behavior of 1 as a two-state system, in which folding pattern 1c is considered to be the "native state" and all other folding patterns comprise the "denatured state", we have been able to carry out van't Hoff analyses of the temperature-dependent conformational changes. In methylene chloride, the native state is enthalpically preferred by 1.9-2.5 kcal/mol but entropically disfavored by 7.4-9.1 eu. Similar values are obtained in chloroform. This thermodynamic characterization demonstrates that, even in a relatively nonpolar environment, the relative enthalpic stabilities of alternative folding patterns cannot be predicted simply by maximizing the pairing of hydrogen-bond donors and acceptors.