Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium
In this paper, we describe the solvent-free three-component synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type compounds from <i>L</i>-tryptophan. The first step of the synthetic methodology involved the esterification of <i>L</i>-tryptophan in excellent...
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| Format: | Article |
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MDPI AG
2020-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/19/4402 |
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| author | Diego Quiroga Lili Dahiana Becerra Ericsson Coy-Barrera |
| author_facet | Diego Quiroga Lili Dahiana Becerra Ericsson Coy-Barrera |
| author_sort | Diego Quiroga |
| collection | DOAJ |
| description | In this paper, we describe the solvent-free three-component synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type compounds from <i>L</i>-tryptophan. The first step of the synthetic methodology involved the esterification of <i>L</i>-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 3<i>H</i>-pyrrol-3-one type intermediates to 1<i>H</i>-pyrrol-3-ol type aromatized rings. |
| first_indexed | 2024-03-10T16:04:11Z |
| format | Article |
| id | doaj.art-f28b9cf85c434a84b503c47ad883b55c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T16:04:11Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f28b9cf85c434a84b503c47ad883b55c2023-11-20T15:02:44ZengMDPI AGMolecules1420-30492020-09-012519440210.3390/molecules25194402Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric EquilibriumDiego Quiroga0Lili Dahiana Becerra1Ericsson Coy-Barrera2Bioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 250247, ColombiaBioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 250247, ColombiaBioorganic Chemistry Laboratory, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada, Campus Nueva Granada, Cajicá 250247, ColombiaIn this paper, we describe the solvent-free three-component synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type compounds from <i>L</i>-tryptophan. The first step of the synthetic methodology involved the esterification of <i>L</i>-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 3<i>H</i>-pyrrol-3-one type intermediates to 1<i>H</i>-pyrrol-3-ol type aromatized rings.https://www.mdpi.com/1420-3049/25/19/44021<i>H</i>-pyrrol-3-olenamines<i>L</i>-tryptophanindole phytoalexinhybrid heterocycles |
| spellingShingle | Diego Quiroga Lili Dahiana Becerra Ericsson Coy-Barrera Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium Molecules 1<i>H</i>-pyrrol-3-ol enamines <i>L</i>-tryptophan indole phytoalexin hybrid heterocycles |
| title | Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium |
| title_full | Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium |
| title_fullStr | Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium |
| title_full_unstemmed | Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium |
| title_short | Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1<i>H</i>-pyrrol-3-ol-type Compounds from <i>L</i>-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3<i>H</i>-pyrrol-3-one↔1<i>H</i>-pyrrol-3-ol Tautomeric Equilibrium |
| title_sort | solvent free three component synthesis of 2 4 5 trisubstituted 1 i h i pyrrol 3 ol type compounds from i l i tryptophan dft b3lyp calculations for the reaction mechanism and 3 i h i pyrrol 3 one 1 i h i pyrrol 3 ol tautomeric equilibrium |
| topic | 1<i>H</i>-pyrrol-3-ol enamines <i>L</i>-tryptophan indole phytoalexin hybrid heterocycles |
| url | https://www.mdpi.com/1420-3049/25/19/4402 |
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