Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry

Catalyst-Free Annulation of Acylethynylpyrroles with 1-Pyrrolines: A Straightforward Access to Tetrahydrodipyrrolo[1,2-a:1′,2′-c]imidazoles

“…Acylethynylpyrroles, readily available via Al 2 O 3 -promoted cross coupling of pyrroles with acylbromoacetylenes (Scheme ), now became a rewarding platform for the synthesis of numerous heterocyclic systems and functionalized enaminones …”

δ-Keto Aminoacrylonitriles and δ-Keto Aminoenones from 1-Pyrrolines, Cyanoacetylenes, and Acetylenic Ketones

“…Functionalized, conjugated aminoacrylonitriles 1 and enaminones, 2 important representatives of enamines, are becoming a focus of research, because they are widely explored in the synthesis of heterocyclic ensembles, and because they are used in medicinal chemistry and materials science. 3 Generally, enamines are valuable therapeutic pharmacophores, the fragments of which are ubiquitous in antibacterial, 4 anticonvulsant, 5 and nonsteroidal anti-inflammatory agents. 6 Conjugated aminoacrylonitriles and aminoenones are employed for the synthesis of azirines, 7 pyrroles, 8 indoles, 9 pyrazoles, 10 imidazoles, 11 oxazoles, 1a pyridines, 12 dihydropyridines, 13 pyrimidines, 14 pyridazines, 15 quinolines, 16 and diverse condensed heterocyclic systems.…”

A Quantum Chemical Study on the Mechanisms of Acylpyrrolylacetylenes Reactions With 1‐Pyrrolines

“…The current interest in functionalized conjugated enaminones is driven by their wide range of applications in the synthesis of heterocyclic ensembles for modern medicinal chemistry and materials science. [4,6] Condensed heterocycle systems containing three five-membered nitrogen heterocycles are attracting attention for their potential pharmaceutical activities, [5] especially for their promising antiviral properties according to in silico evaluations. [7] Here we investigate the reactions' mechanisms by using the interaction of the 1-phenyl-3-(1H-pyrrol-2-yl) prop-2-yn-1-one (1) and 5-methyl-3,4-dihydro-2H-pyrrole (2) in acetonitrile and methanol as an illustrative example.…”

“…Both of these recently discovered reactions are of undoubted value for fundamental organic chemistry and also appear to be promising in terms of practical applications. The current interest in functionalized conjugated enaminones is driven by their wide range of applications in the synthesis of heterocyclic ensembles for modern medicinal chemistry and materials science [4,6] . Condensed heterocycle systems containing three five‐membered nitrogen heterocycles are attracting attention for their potential pharmaceutical activities, [5] especially for their promising antiviral properties according to in silico evaluations [7]…”