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Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds

“…This rapid Mannich-type addition provides an intermediate capable of intramolecular lactamization to form the α-ketolactam that subsequently tautomerizes to the observed multicomponent product 4 . The mechanism is supported through the observations that preformed electron-deficient imines do not undergo this mild reaction in agreement with literature reports that require harsh reaction conditions for such reactions. − It is also possible that upon imine protonation a more concerted (albeit asynchronous) process ensues as we do not observe the amino ester in any of the reaction mixtures. Further exploration in the reaction mechanism and efforts to render it asymmetric are ongoing.…”

“…Among the various multicomponent approaches to access highly functionalized heterocycles, including pyrrolidinones, imines serve as a common intermediate. − In addition to our efforts, there has been a long history of elegant methods toward these versatile building blocks. Gein and co-workers have contributed significant efforts to the synthesis of these molecules via a similar multicomponent reaction that requires an acyl electron-withdrawing group and prolonged reaction time. − A number of other groups have used analogous strategies, all employing activated precursors and aggressive reaction conditions. − Joo and co-workers and Yavari and Souri independently synthesized related pyrrolidinones utilizing symmetrical alkynes. , …”

Three-Component Condensation of Methyl Acylpyruvates with Aromatic Aldehydes and Ethylenediamine. Chemical Properties of the Products

“…It is also known that three-component reaction between an acylpyruvic acid ester, aromatic aldehyde, and ethylenediamine leads to formation of 4,5-disubstituted 1-(2-aminoethyl)-3-hydroxy-2,5-dihydro-1H-pyrrol-2ones [2]. It seemed reasonable to examine how the reactant ratio affects the direction of the above threecomponent condensation.…”

Reaction of acylpyruvate esters with a mixture of aromatic aldehyde and 1,3-diaminopropane and pharmacological activity of the products

“…It was shown previously that reaction of acylpyruvate esters with a mixture of aromatic aldehyde and ethylenediamine in equimolar amounts formed substituted 1-(2-aminoethyl)-3-hydroxy-3-pyrrolin-2-ones [1]. It is known that substituted 3-hydroxy-3-pyrrolin-2-ones possess various types of pharmacological activity such as anti-inflammatory [2], analgesic [3], antiviral [4], and nootropic [3].…”