Aqueous/Nonaqueous DBU Mixtures: Versatile Switching Media for Chemoselective Aldol, Baylis‐Hillman, and Aldol Condensation Reactions

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

Abstract Isophorone is a relatively small molecule with several neighboring reacting sites, making it susceptible to various competing reactions aldehydes, including aldol, Baylis‐Hillman (BH), aldol condensation, and Michael addition reactions. In the present work, we have designed switchable 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐catalyzed procedure, where reaction of isophorone aldehydes guided chemoselectively toward either BH, or condensation reactions, depending on use water and/or heat. This controllable divergency likely stems from ability tune dual nucleophilicity/basicity characters DBU/H 2 O medium. other words, nucleophilicity DBU plays crucial role in directing process formation BH adducts absence water. At same time, pathway dominates when present. The conditions were amenable for tandem processes, as demonstrated an condensation/Diels‐Alder sequence.

Язык: Английский

Photocatalytic Three-Component Assemblies of Enaminones, α-Diazo Esters, and Nitriles for the Synthesis of N,N-Diacylated Glycine Esters

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A facile method with simple starting materials, including enaminones, α-diazo esters, and nitriles, has been developed for the direct synthesis of N,N-diacyl glycine esters via visible light photocatalysis. The reaction involves a novel carbon-carbon bond cleavage in leading to products high tolerance variability substructures among all three components.

Язык: Английский

Modular synthesis of unsymmetrical indolyl diketones from ynediones via sequential aza-Micheal addition/C-H functionalization

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Herein, we disclose an efficient approach for the synthesis of unsymmetrical indolyl diketones from easily accessible 1,2-alkynediones involving a sequential aza-Michael addition/C-H Functionalization process. The two-step, one-pot strategy involves addition aniline generating

Язык: Английский