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Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations.
Beilstein J Org Chem
July 2024
Institute of Functional Materials Chemistry, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Nauky Ave., 60, 61072, Kharkiv, Ukraine.
By one-pot four- and three-component Ugi reactions involving convertible isocyanides and unexplored pyrrole-containing β-chlorovinylaldehyde, a small library of 20 bisamides with unusual behavior in post-Ugi transformations was prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of heterylidenepyruvic acid. An optimized synthetic protocol for this transformation was elaborated and a plausible sequence involving the elimination of the 2-chloroacetamide moiety and the conversion of the β-chlorovinyl fragment into a vinyl one is provided.
View Article and Find Full Text PDFPalladium-Catalyzed Domino Heck/Cross-Coupling Cyclization Reaction: Diastereoselective Synthesis of Furan-Containing Indolines.
J Org Chem
June 2024
Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, Hubei 430070, China.
Herein, a palladium-catalyzed diastereoselective dearomatization/cross-coupling cyclization reaction between -arylacyl indoles and ()-β-chlorovinyl ketones is reported. Through this cyclization/cycloisomerization cascade, a series of furan-containing indolines were obtained in yields up to 95%. The reaction features readily accessible starting materials, benzyl Pd(II)-catalyzed cycloisomerization of ()-β-chlorovinyl ketones, the sequential formation of three bonds and bis-heterocycles, and excellent diastereoselectivity.
View Article and Find Full Text PDFChemodivergent Sulfonylation of Enynones via Ionic and Radical Addition Modes of Sulfinic Acids.
Org Lett
August 2023
Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Different addition modes of sulfinic acids were developed for the chemodivergent sulfonylation of enynones, where the ionic sulfonylation to an alkyne moiety of enynones was effected through a salt-controlled -addition pathway. The radical sulfonylation of an alkene moiety also provided the stereodefined sulfonylated alkenes. A one-pot tandem sequence of the Ti(O-Pr)-catalyzed α-vinyl aldol condensation of ()-β-chlorovinyl ketones followed by the chemodivergent sulfonylations was also explored, allowing for ready access to highly substituted dienes and enynes.
View Article and Find Full Text PDFOne-Pot Tandem Nickel-Catalyzed α-Vinyl Aldol Reaction and Cycloaddition Approach to [1,2,3]Triazolo[1,5-]quinolines.
Org Lett
January 2023
Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
A one-pot tandem approach to [1,2,3]triazolo[1,5-]quinolines was developed from ()-β-chlorovinyl ketones and 2-azidoaryl carbonyls using a sequence of α-vinyl aldol and azide-alkyne cycloaddition reactions. In particular, the intramolecular azide-alkyne cycloaddition of allenol intermediates was readily promoted by a synergistic action of NEt and nickel catalysts. Given that the [1,2,3]triazolo[1,5-]quinolines are useful synthetic precursors to α-diazoimines through ring-chain isomerization process, the subsequent denitrogenative transformations should provide ready access to valuable heterocyclic compounds.
View Article and Find Full Text PDFPhotoinduced Chloroamination Cyclization Cascade with -Chlorosuccinimide: From -(Allenyl)sulfonylamides to 2-(1-Chlorovinyl)pyrrolidines.
J Org Chem
May 2023
Department of Chemistry, University of Torino, Via P. Giuria 7, 10125, Turin, Italy.
Here, we present an intriguing photoinduced chloroamination cyclization of allenes bearing a tethered sulfonylamido group to afford 2-(1-chlorovinyl)pyrrolidines and related heterocycles in the presence of -chlorosuccinimide (NCS) as the chlorine source. An in depth experimental and computational mechanistic study revealed the existence of multiple reaction pathways leading to a common nitrogen centered radical (NCR). This key NCR can be, in fact, originated from (a) the oxidation of the deprotonated allene by the photoexcited state of the Ru-catalyst and (b) the photodissociation of the in situ formed -chloroallene.
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