Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids

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

“…[8,13] We believe that a double conjugate adduct could be achieved if a second molecule of acetylenedicarboxylate was added to the reaction system, and that this adduct might be useful as a potential synthon for tandem reactions. Recently, the AgBF 4 -catalyzed addition and oxidative cyclization of two molecules of alkynoates with benzylamine to give polysubstituted pyrroles [14] and the onepot sequential reaction of benzoylacetylene with 2-furylmethylamine to give 1,4-dihydropyridines [15] have been reported as two successful examples of this synthetic methodology.…”

“…[3c,6] In fact, the Huisgen addition is also a convenient method for the preparation of β-enaminones and esters by adding aliphatic and aromatic amines to activated alkynes with carbonyl groups. [7,8] The domino reactions of a primary amine, an acetylenedicarboxylate, and a third component have provided elegant procedures for the synthesis of various N-and N,O-heterocycles. [9][10][11] Recently, we have found that the four-component reactions of arylamines, acetylenedicarboxylate, aromatic aldehydes, and acetonitrile derivatives provide an efficient and practical method for the synthesis of 1,4-dihydropyridines.…”

A Metal‐Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5‐Disubstituted 1,2,3‐Triazoles

“…Theoretically, the enaminone compounds 4 may exist as three tautomers: the iminoenol 4 a, iminoketone 4 b, and ketoenamine 4 c. [9] The a-diazo iminoketone 7 [9] and 1-tosyl triazole 8 [5] could be obtained from the Regitz diazo transfer of 4 b and 1,3-dipolar cycloaddition of 4 c with TsN 3 , respectively. We assumed that, in the presence of suitable bases, 4 a might react with TsN 3 to give the a-diazoimine intermediate 6, which could further cyclize to afford the triazole 5 (Scheme 2).…”

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

“…Among the electron-rich dienophiles, vinyl enol ethers, vinyl enamides, vinyl sulfides, cyclopentadienes, indenes, alkynes and enamines have been mostly used in this method [12–22]. β-Enamino esters [23–26], which may be readily generated in situ by the addition of a primary amine to electron-deficient alkynes, such as methyl propiolate or dimethyl acetylenedicarboxylate [27–30], have shown versatile reactivity and have been widely used as key intermediates in a number of domino reactions to construct heterocyclic systems [31–42]. However, a survey of literature reveals that a Povarov reaction with in situ generated β - enamino ester as dienophile has not been reported until now.…”