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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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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. |
format | Online Article Text |
id | pubmed-6197048 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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