Synthesis of substituted pyrroles in the glaser reaction

Vizer, S. A.; Yerzhanov, K. B.; Dembitsky, Valery M.

doi:10.1002/hc.20184

Cited by 7 publications

(2 citation statements)

References 35 publications

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“…With propargylated enamines 5a – j in hand, we next envisioned a regioselective 5- exo - dig hydroamination reaction leading to phosphonylated pyrroles. A literature search resulted in a copious amounts of references regarding hydroamination catalysts, solvents, and the substrate scope for the synthesis of pyrroles. − Based on our own work regarding transition-metal-catalyzed cyclization reactions, − several Au catalysts were evaluated at first with 5a , albeit with mediocre results (Table , entries a–c). Hydrolysis of the enamine took place along with some formation of the desired pyrrole 6a .…”

Section: Resultsmentioning

confidence: 99%

Preparation of Tetrasubstituted 3-Phosphonopyrroles through Hydroamination: Scope and Limitations

2014

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Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available β-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.

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Section: Resultsmentioning

confidence: 99%

Preparation of Tetrasubstituted 3-Phosphonopyrroles through Hydroamination: Scope and Limitations

2014

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“…The synthesis of diacetylenes, substituted pyrroles and cumulenes was reported by Vizer and Yerzhanov using the modied Glaser type reaction conditions. 45 Two products viz. 2,5dimethyl-3-acetylpyrrole and the corresponding dipyrrole were formed during the oxidative dimerisation of 1,3-diketone in water-ethanol solution of ammonium chloride in the presence of CuCl 2 and oxygen (Scheme 23).…”

Section: -Propargyl-13-dicarbonyl Compoundsmentioning

confidence: 99%