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Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3H-pyrrol-3-one↔1H-pyrrol-3-ol Tautomeric Equilibrium

Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 250247, Colombia
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Molecules 2020, 25(19), 4402; https://doi.org/10.3390/molecules25194402
Received: 2 September 2020 / Revised: 19 September 2020 / Accepted: 24 September 2020 / Published: 25 September 2020
(This article belongs to the Section Organic Chemistry)
In this paper, we describe the solvent-free three-component synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type compounds from L-tryptophan. The first step of the synthetic methodology involved the esterification of L-tryptophan in excellent yields (93–98%). Equimolar mixtures of alkyl 2-aminoesters, 1,3-dicarbonyl compounds, and potassium hydroxide (0.1 eq.) were heated under solvent-free conditions. The title compounds were obtained in moderate to good yields (45%–81%). Density functional theory using “Becke, 3-parameter, Lee–Yang–Parr” correlational functional (DFT-B3LYP) calculations were performed to understand the molecular stability of the synthesized compounds and the tautomeric equilibrium from 3H-pyrrol-3-one type intermediates to 1H-pyrrol-3-ol type aromatized rings. View Full-Text
Keywords: 1H-pyrrol-3-ol; enamines; L-tryptophan; indole phytoalexin; hybrid heterocycles 1H-pyrrol-3-ol; enamines; L-tryptophan; indole phytoalexin; hybrid heterocycles
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MDPI and ACS Style

Quiroga, D.; Becerra, L.D.; Coy-Barrera, E. Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3H-pyrrol-3-one↔1H-pyrrol-3-ol Tautomeric Equilibrium. Molecules 2020, 25, 4402. https://doi.org/10.3390/molecules25194402

AMA Style

Quiroga D, Becerra LD, Coy-Barrera E. Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3H-pyrrol-3-one↔1H-pyrrol-3-ol Tautomeric Equilibrium. Molecules. 2020; 25(19):4402. https://doi.org/10.3390/molecules25194402

Chicago/Turabian Style

Quiroga, Diego; Becerra, Lili D.; Coy-Barrera, Ericsson. 2020. "Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3H-pyrrol-3-one↔1H-pyrrol-3-ol Tautomeric Equilibrium" Molecules 25, no. 19: 4402. https://doi.org/10.3390/molecules25194402

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