Catalytic properties of 4,5-bridged proline methano- and ethanologues in the Hajos–Parrish intramolecular aldol reaction

Hocine, Sofiane; Berger, Gilles; Houk, K. N.; Hanessian, Stephen

doi:10.1039/d1qo01688a

Cited by 3 publications

(2 citation statements)

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“…The Gibbs free energy of all intermediate compounds, the rate constant (k) and the half-life (t 1/2 ) of the reaction were calculated, respectively. [47][48][49][50][51] As shown in Fig. 5, MPD-O undergoing intramolecular nucleophilic addition to form TS1 through Int1 was the same step for both pathways A and B.…”

Section: Resultsmentioning

confidence: 85%

In situ fluorescence visualizing of a temperature-dependent photoreaction process of pyridazine N-oxide

Gong

et al. 2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 85%

In situ fluorescence visualizing of a temperature-dependent photoreaction process of pyridazine N-oxide

Gong

et al. 2023

Org. Chem. Front.

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“…As an academic, it has been rewarding that cis- and trans- 4,5-methano prolines have rendered valuable service to the development of marketed drugs and to new prototypes that are currently being exploited in ongoing clinical trials many years after publication of our results. Other applications of 4,5-methano L-proline in the context of synthetic methodology, catalysis, − and PP2 type helical oligomers have been reported from our group.…”

Section: Medicinal Chemistry-inspired Collaborations With Industry Ma...mentioning

confidence: 80%

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

Hanessian

2024

J. Org. Chem.

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L-Proline Catalyzed Knoevenagel Condensation of Aldehydes with Active Methylene Compounds and Their Molecular Modeling Studies for Anti-SARS CoV-2 Potentials

Thorat

Nagre

Dhurandhar

et al. 2022

CEI

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Introduction: An efficient one-pot synthesis of 2-alkylidene/arylidene derivatives was reported from active methylene compounds such as malononitrile/ethyl cyanoacetate/5-methyl-2,4-dihydro-3H-pyrazol-3-one and aldehydes in the presence of 10 mol% of L-proline (ethanol at room temperature). Methods: All derivatives were obtained in good to excellent yields. The structures of the synthesized compounds were confirmed from their FTIR (Fourier-transform infrared spectroscopy), 1H-NMR (Proton nuclear magnetic resonance), and mass spectroscopy. The importance of these compounds is predicted from their SAR (structure-activity relationship) study. Moreover, these newer compounds were further docked into various therapeutic targets of the SARS-CoV-2 (severe acute respiratory syndrome–related coronavirus) virus. Results: Results from our molecular docking suggested that these compounds have good inhibitory properties on the SARS- CoV-2 virus. Conclusion: L-proline (bifunctional organic catalyst) is found to be the best catalyst for the synthesis of different condensed products from active methylene compounds and aldehydes.

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Catalytic properties of 4,5-bridged proline methano- and ethanologues in the Hajos–Parrish intramolecular aldol reaction

Abstract: The catalysis of the Hajos–Parrish reaction by cis- and trans-4,5-ethano-proline was explored experimentally and computationally with DFT (ωB97X-D and MN15) and DLPNO-CCSD(T).

Cited by 3 publications

References 60 publications

In situ fluorescence visualizing of a temperature-dependent photoreaction process of pyridazine N-oxide

In situ fluorescence visualizing of a temperature-dependent photoreaction process of pyridazine N-oxide

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

L-Proline Catalyzed Knoevenagel Condensation of Aldehydes with Active Methylene Compounds and Their Molecular Modeling Studies for Anti-SARS CoV-2 Potentials

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