Molecular Diversity of Three‐Component Reactions of Aromatic Aldehydes, Arylamines, and Acetylenedicarboxylates

Abstract

The three-component reactions of aromatic aldehydes, arylamines, and acetylenedicarboxylates show very interesting molecular diversity. In an aqueous ethanol solution the threecomponent reaction gave polysubstituted 2-hydroxyhydropyridines. In absolute ethanol 1,4-dihydropyridines were

Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines

“…When 95% EtOH was employed, 2-hydroxylhydropyridines 26 were obtained diastereoselectively probably by the addition of H 2 O to 25 (Scheme 12). 24 Scheme 5 Enal-based enantioselective synthesis of 1,4-DHPs.…”

Efficient Synthesis of the Functionalized Spiro[indoline‐3,4′‐pyridine] via Four‐component Reaction

“…[10][11][12][13][14][15][16][17][18][19][20][21] Recently multicomponent reactions based on the sequential reactions of isatins [22,23] or benzofuran-2,3-diones [24,25] with Huisgen's 1,4-dipoles, which were formed in situ from the addition of azaarenes with electron-deficient alkynes have been successfully used to construct versatile spirooxindole systems. [27] As a part of our program on the study of the reactivity of active β-enamino esters derived from the reaction of electrondeficient alkynes with primary arylamines, [28][29][30] herein we wish to report the efficient synthesis of the novel spiro[indoline-3,4'-pyridine] derivatives via four-component reaction of arylamine, acetylenedicarboxylate, isatins and malononitrile. [26] Recently Balalaie and coworkers also reported this four-compoenent reaction for the synthesis of 1,4-dihydropyridines by using (NH 4 ) 2 HPO 4 as a base in aqueous media.…”

Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids

“…7–9 Typical conditions involve polar solvents such as dioxane, THF, or EtOH with less reactive amine substrates heated in AcOH or DMF in the presence of TMSCl; unfortunately, aliphatic aldehydes are scarcely employed and usually provide low yields of pyrrolone products. 5a,7–10 An alternate multicomponent approach 11 as well as asymmetric protocols for the synthesis of 3-hydroxy-1,5-dihydro -2H -pyrrol-2-ones were also recently described. 12 In this work, we investigated 3-hydroxy-1,5-dihydro -2H -pyrrol-2-ones as high-value building blocks for more densely functionalized heterocycles and natural products and therefore sought optimized methods for their preparation.…”