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Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach

We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole...

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Autores principales: Zbancioc, Gheorghita, Ciobanu, Catalina-Ionica, Mangalagiu, Ionel I., Moldoveanu, Costel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9147717/
https://www.ncbi.nlm.nih.gov/pubmed/35630657
http://dx.doi.org/10.3390/molecules27103180
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author Zbancioc, Gheorghita
Ciobanu, Catalina-Ionica
Mangalagiu, Ionel I.
Moldoveanu, Costel
author_facet Zbancioc, Gheorghita
Ciobanu, Catalina-Ionica
Mangalagiu, Ionel I.
Moldoveanu, Costel
author_sort Zbancioc, Gheorghita
collection PubMed
description We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430–445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides.
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spelling pubmed-91477172022-05-29 Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach Zbancioc, Gheorghita Ciobanu, Catalina-Ionica Mangalagiu, Ionel I. Moldoveanu, Costel Molecules Article We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430–445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides. MDPI 2022-05-16 /pmc/articles/PMC9147717/ /pubmed/35630657 http://dx.doi.org/10.3390/molecules27103180 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zbancioc, Gheorghita
Ciobanu, Catalina-Ionica
Mangalagiu, Ionel I.
Moldoveanu, Costel
Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title_full Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title_fullStr Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title_full_unstemmed Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title_short Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach
title_sort ultrasound-assisted synthesis of fluorescent azatetracyclic derivatives: an energy-efficient approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9147717/
https://www.ncbi.nlm.nih.gov/pubmed/35630657
http://dx.doi.org/10.3390/molecules27103180
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