- Protecting-group-free synthesis of hydroxyesters from amino alcohols
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The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported. The formation of a transient diazonium species with a dinitrite reagent is key in this transformation. The reaction conditions are compatible with a variety of functional groups.
- Joseph-Valcin, Eve-Marline,Lebel, Hélène,Reynard, Guillaume
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supporting information
p. 10938 - 10941
(2020/10/02)
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- Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
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A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
- da Silva, Amanda F.,Afonso, Marco A. S.,Cormanich, Rodrigo A.,Jurberg, Igor D.
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p. 5648 - 5653
(2020/04/22)
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- Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2
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The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.
- Yan, Si-Shun,Zhu, Lei,Ye, Jian-Heng,Zhang, Zhen,Huang, He,Zeng, Huiying,Li, Chao-Jun,Lan, Yu,Yu, Da-Gang
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p. 4873 - 4878
(2018/06/07)
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- Molecular Modification of Anticholinergics as Probes for Muscarinic Receptors. Amino Esters of α-Substituted Phenylacetic Acid and Related Analogues
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Two series of compounds having the general structure of C6H5CRR'COOCH2CH2NEt2 were synthesized and examined for their antispasmodic activities.These compounds were selected as structural probes for exploring the nature of muscarinic cholinergic receptor binding sites that interact with atropine-like anticholinergics.These studies indicate a rather strict size limitation for the hydrophobic region of the receptor and suggest intramolecular hydrogen bonding as a possible means to explain the observed stereoselectivity.
- Lu, Mattias C.,Wung, Walley E.,Shih, Lisa B.,Callejas, Soledad,Gearien, James E.,Thompson, Emmanuel B.
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p. 273 - 278
(2007/10/02)
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