82091-12-1Relevant academic research and scientific papers
HETEROCYCLIC WDR5 INHIBITORS AS ANTI-CANCER COMPOUNDS
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Page/Page column 76, (2021/02/19)
The present invention provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof; (I) which are inhibitors of WDR5. The present invention also provides pharmaceutical compositions comprising such compounds, compositions comprising such compounds with an additional therapeutic agent and the therapeutic uses of such compounds.
ASK1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF
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Paragraph 0347, (2020/01/02)
The present disclosure relates to a compound as shown in formula (II), a tautomer or a pharmaceutically acceptable salt thereof, and disclosed is the use thereof in preparing a drug for treating an ASK1-associated disease.
Tandem buildup of complexity of aromatic molecules through multiple successive electrophile generation in one pot, controlled by varying the reaction temperature
Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 1680 - 1693 (2016/02/09)
While some sequential electrophilic aromatic substitution reactions, known as tandem/domino/cascade reactions, have been reported for the construction of aromatic single skeletons, one of the most interesting and challenging possibilities remains the one-pot build-up of a complex aromatic molecule from multiple starting components, i.e., ultimately multi-component electrophilic aromatic substitution reactions. In this work, we show how tuning of the leaving group ability of phenolate derivatives from carbamates and esters provides a way to successively generate multiple unmasked electrophiles in a controlled manner in one pot, simply by varying the temperature. Here, we demonstrate the autonomous formation of up to three bonds in one pot and formation of two bonds arising from a three-component electrophilic aromatic substitution reaction. This result provides a proof-of-concept of our strategy applicable for the self-directed construction of complex aromatic structures from multiple simple molecules, which can be a potential avenue to realize multi-component electrophilic aromatic substitution reactions.
Protonation switching to the least-basic heteroatom of carbamate through cationic hydrogen bonding promotes the formation of isocyanate cations
Kurouchi, Hiroaki,Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
, p. 8682 - 8690 (2014/07/21)
We found that phenethylcarbamates that bear ortho-salicylate as an ether group (carbamoyl salicylates) dramatically accelerate O-C bond dissociation in strong acid to facilitate generation of isocyanate cation (N-protonated isocyanates), which undergo subsequent intramolecular aromatic electrophilic cyclization to give dihydroisoquinolones. To generate isocyanate cations from carbamates in acidic media as electrophiles for aromatic substitution, protonation at the ether oxygen, the least basic heteroatom, is essential to promote C-O bond cleavage. However, the carbonyl oxygen of carbamates, the most basic site, is protonated exclusively in strong acids. We found that the protonation site can be shifted to an alternative basic atom by linking methyl salicylate to the ether oxygen of carbamate. The methyl ester oxygen ortho to the phenolic (ether) oxygen of salicylate is as basic as the carbamate carbonyl oxygen, and we found that monoprotonation at the methyl ester oxygen in strong acid resulted in the formation of an intramolecular cationic hydrogen bond (>C=O+-H...O) with the phenolic ether oxygen. This facilitates O-C bond dissociation of phenethylcarbamates, thereby promoting isocyanate cation formation. In contrast, superacid-mediated diprotonation at the methyl ester oxygen of the salicylate and the carbonyl oxygen of the carbamate afforded a rather stable dication, which did not readily undergo C-O bond dissociation. This is an unprecedented and unknown case in which the monocation has greater reactivity than the dication.
METHOD OF PREPARING ESTER-SUBSTITUTED DIARYL CARBONATES
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Page/Page column 14, (2008/06/13)
An improved method for the preparation of ester-substituted diaryl carbonates prepared by reacting phosgene with recycle streams of ester-substituted phenols from reaction processes using a tetraalkyl ammonium hydroxide catalyst, a tetraalkyl phosphonium
Method of preparing ester-substituted diaryl carbonates
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Page/Page column 6; 7, (2008/06/13)
The present invention relates to an interfacial method of preparing ester-substituted diaryl carbonates. The method includes the steps of: forming a reaction mixture comprising phosgene, an ester-substituted phenol, an organic solvent, and a catalyst sele
Interfacial method of preparing ester-substituted diaryl carbonates
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, (2008/06/13)
High yields of ester-substituted diary carbonates such as bis-methyl salicyl carbonate were obtained by the condensation of methyl salicylate with phosgene in the presence of a phase transfer catalyst (PTC) in an interfacial reaction system in which the p
