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One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor

The use of a modified prototype continuous flow reactor (CFR) as a pivotal part of a number of versatile singlet oxygen‐mediated reaction sequences is presented herein. These sequences target rapid access to structural complexity and diversity. The prototype reactor achieves high conversions and pro...

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Autores principales: Ioannou, Georgios I., Montagnon, Tamsyn, Kalaitzakis, Dimitris, Pergantis, Spiros A., Vassilikogiannakis, Georgios
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6197048/
https://www.ncbi.nlm.nih.gov/pubmed/30393758
http://dx.doi.org/10.1002/cptc.201800068
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author Ioannou, Georgios I.
Montagnon, Tamsyn
Kalaitzakis, Dimitris
Pergantis, Spiros A.
Vassilikogiannakis, Georgios
author_facet Ioannou, Georgios I.
Montagnon, Tamsyn
Kalaitzakis, Dimitris
Pergantis, Spiros A.
Vassilikogiannakis, Georgios
author_sort Ioannou, Georgios I.
collection PubMed
description The use of a modified prototype continuous flow reactor (CFR) as a pivotal part of a number of versatile singlet oxygen‐mediated reaction sequences is presented herein. These sequences target rapid access to structural complexity and diversity. The prototype reactor achieves high conversions and productivities by attaining large specific surface areas for these biphasic reactions. In the reactor, the reaction solution is nebulized (using either oxygen or air) and the resulting aerosol is irradiated by an LED jacket that surrounds the Pyrex reaction chamber. The one pot procedures developed herein are, according to many different criteria, both highly efficient and green. The key common intermediates and the source of both the complexity and variety of the final products are N‐acyl imminium ions (NAI; protonated N‐acyl enamines). The initial substrates are simple and readily accessible furans and the diverse array of products is composed of different complex γ‐lactams. Many of the products are of particular interest due to their close relationships to known biologically active molecules.
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spelling pubmed-61970482018-10-31 One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor Ioannou, Georgios I. Montagnon, Tamsyn Kalaitzakis, Dimitris Pergantis, Spiros A. Vassilikogiannakis, Georgios ChemPhotoChem Communications The use of a modified prototype continuous flow reactor (CFR) as a pivotal part of a number of versatile singlet oxygen‐mediated reaction sequences is presented herein. These sequences target rapid access to structural complexity and diversity. The prototype reactor achieves high conversions and productivities by attaining large specific surface areas for these biphasic reactions. In the reactor, the reaction solution is nebulized (using either oxygen or air) and the resulting aerosol is irradiated by an LED jacket that surrounds the Pyrex reaction chamber. The one pot procedures developed herein are, according to many different criteria, both highly efficient and green. The key common intermediates and the source of both the complexity and variety of the final products are N‐acyl imminium ions (NAI; protonated N‐acyl enamines). The initial substrates are simple and readily accessible furans and the diverse array of products is composed of different complex γ‐lactams. Many of the products are of particular interest due to their close relationships to known biologically active molecules. John Wiley and Sons Inc. 2018-05-02 2018-10 /pmc/articles/PMC6197048/ /pubmed/30393758 http://dx.doi.org/10.1002/cptc.201800068 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Ioannou, Georgios I.
Montagnon, Tamsyn
Kalaitzakis, Dimitris
Pergantis, Spiros A.
Vassilikogiannakis, Georgios
One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title_full One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title_fullStr One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title_full_unstemmed One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title_short One‐Pot Synthesis of Diverse γ‐Lactam Scaffolds Facilitated by a Nebulizer‐Based Continuous Flow Photoreactor
title_sort one‐pot synthesis of diverse γ‐lactam scaffolds facilitated by a nebulizer‐based continuous flow photoreactor
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6197048/
https://www.ncbi.nlm.nih.gov/pubmed/30393758
http://dx.doi.org/10.1002/cptc.201800068
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