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Molecules
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Advances in the Synthesis of Heterocyclic Compounds and Their Applications
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Advances in the Synthesis of Heterocyclic Compounds and Their Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 30 September 2024 | Viewed by 3092

Special Issue Editors

Dr. Mircea Darabantu

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Chemistry and Chemical Engineering, University Babes-Bolyai Cluj-Napoca, 11 Aranyi Janos Str., 400028 Cluj-Napoca, Romania
Interests: organic chemistry synthesis; heterocyclic chemistry; medicinal and pharmaceutical chemistry; nuclear magnetic resonance; natural product chemistry; organometallics; dendritic chemistry; stereochemistry
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Ionel Mangalagiu

E-Mail Website
Guest Editor
Chemistry Department, Alexandru Ioan Cuza University of Iasi, 700506 Iasi, Romania
Interests: heterocycles; medicinal chemistry; anticancer; antituberculosis; microwave; ultrasounds; organic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In hopes of attracting your attention, the new topic, “Advances in the Synthesis of Heterocyclic Compounds and Their Applications”, aims to expand our scientific knowledge about the current world by exploring the frontiers between at least two of their lively interfaces: human life and the environment.

In this view, our previous traditional strategies, “heteroring synthesis” and “substituent modification” (including their combination), require an update of their meaning by two actual conceptual approaches, namely “covalent” vs. “non-covalent” with reference to all types of heteromolecules, from the smallest to (supramolecular) 2(3)D nano-architectures (dendrimers, MOFs, COFs, etc.) without neglecting the still “exotic” molecular machines.

Subject to all evolutionary facets of heterocyclic chemistry, the perpetual developments reimagined within the current organic heterosynthesis (strategies, methodologies, reaction mechanisms, reagents, catalysts, chemical and instrumental auxiliaries) nevertheless obey two crucial common denominators, “selectivity” vs. “specificity” (these terms being, equally, preceded by typical prefixes, either chemo-, regio-, or stereo-), as mandatory criteriums.

This Special Issue of “Molecules” is intended to gather research articles, communications, and review papers capable of providing an overview of the latest progresses in synthetic methodologies and chemical technologies targeting heteromolecules, mainly those related to their near future defined as “atomic precision” in chemical reactivity. The sustainability of these efforts, involving intrinsic chemical diversity, is expected to highlight innovative applications of heterocyclic compounds to human life and the environment.

Dr. Mircea Darabantu
Prof. Dr. Ionel Mangalagiu
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • biomimetics and new chemical entities (NCEs)
  • domino reactions
  • "intelligent" molecule
  • iterative synthesis
  • multicomponent reactions
  • organic (Nano)materials
  • organo-catalytic systems
  • selective processes
  • total synthesis, unconventional methods and techniques

Published Papers (4 papers)

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Research

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24 pages, 7455 KiB  
Article
New Library of Iodo-Quinoline Derivatives Obtained by an Alternative Synthetic Pathway and Their Antimicrobial Activity
by Cristina Maria Al-Matarneh, Alina Nicolescu, Ioana Cristina Marinaş, Mădalina Diana Găboreanu, Sergiu Shova, Andrei Dascălu, Mihaela Silion and Mariana Pinteală
Molecules 2024, 29(4), 772; https://doi.org/10.3390/molecules29040772 - 07 Feb 2024
Cited by 1 | Viewed by 560
Abstract
6-Iodo-substituted carboxy-quinolines were obtained using a one-pot, three-component method with trifluoroacetic acid as a catalyst under acidic conditions. Iodo-aniline, pyruvic acid and 22 phenyl-substituted aldehydes (we varied the type and number of radicals) or O-heterocycles, resulting in different electronic effects, were the starting [...] Read more.
6-Iodo-substituted carboxy-quinolines were obtained using a one-pot, three-component method with trifluoroacetic acid as a catalyst under acidic conditions. Iodo-aniline, pyruvic acid and 22 phenyl-substituted aldehydes (we varied the type and number of radicals) or O-heterocycles, resulting in different electronic effects, were the starting components. This approach offers advantages such as rapid response times, cost-effective catalysts, high product yields and efficient purification procedures. A comprehensive investigation was conducted to examine the impact of aldehyde structure on the synthesis pathway. A library of compounds was obtained and characterized by FT-IR, MS, 1H NMR and 13C NMR spectroscopy and single-ray crystal diffractometry. Their antimicrobial activity against S. epidermidis, K. pneumonie and C. parapsilosis was tested in vitro. The effect of iodo-quinoline derivatives on microbial adhesion, the initial stage of microbial biofilm development, was also investigated. This study suggests that carboxy-quinoline derivatives bearing an iodine atom are interesting scaffolds for the development of novel antimicrobial agents. Full article
(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications)
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23 pages, 20060 KiB  
Article
A Convenient Synthesis of Novel Isoxazolidine and Isoxazole Isoquinolinones Fused Hybrids
by Konstantinos A. Ouzounthanasis, Stergios R. Rizos and Alexandros E. Koumbis
Molecules 2024, 29(1), 91; https://doi.org/10.3390/molecules29010091 - 22 Dec 2023
Viewed by 782
Abstract
Isoxazolidine, isoxazole, and isoquinolinone rings are present in the structure of several natural products and/or pharmaceutically interesting compounds. In this work, facile and efficient pathways have been developed for the preparation of fused frameworks bearing those heterocycles. The successful approaches for both isoxazolidine/isoquinolinone [...] Read more.
Isoxazolidine, isoxazole, and isoquinolinone rings are present in the structure of several natural products and/or pharmaceutically interesting compounds. In this work, facile and efficient pathways have been developed for the preparation of fused frameworks bearing those heterocycles. The successful approaches for both isoxazolidine/isoquinolinone and isoxazole/isoquinolinone hybrid syntheses relied initially on 1,3-dipolar cycloadditions of nitrones and nitrile oxides to indenone and 2-propargylbenzamide, respectively. The construction of the isoquinolinone lactam system followed by performing a selective Schmidt reaction for isoxazolidine derivatives (two steps overall), whereas the isoxazole lactams were reached via an Ullmann-type cyclisation (three steps overall). Key observations were made regarding the stereo- and regioselectivities of the reactions employed, and small libraries of the targeted hybrids were prepared, demonstrating the general applicability of these strategies. Full article
(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications)
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14 pages, 3755 KiB  
Article
1,1,1,3,3,3-Hexafluoro-2-Propanol-Promoted Friedel–Crafts Reaction: Metal-Free Synthesis of C3-Difluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines at Room Temperature
by Juanjuan Gao, Zhaowen Liu, Xiaohua Guo, Longhui Wu, Zhixi Chen and Kai Yang
Molecules 2023, 28(22), 7522; https://doi.org/10.3390/molecules28227522 - 10 Nov 2023
Cited by 2 | Viewed by 648
Abstract
A facile and efficient method has been developed for the synthesis of C3-difluoromethyl carbinol-containing imidazo[1,2-a]pyridines at room temperature via the HFIP-promoted Friedel–Crafts reaction of difluoroacetaldehyde ethyl hemiacetal and imidazo[1,2-a]pyridines. This strategy could be applied to the direct C(sp2 [...] Read more.
A facile and efficient method has been developed for the synthesis of C3-difluoromethyl carbinol-containing imidazo[1,2-a]pyridines at room temperature via the HFIP-promoted Friedel–Crafts reaction of difluoroacetaldehyde ethyl hemiacetal and imidazo[1,2-a]pyridines. This strategy could be applied to the direct C(sp2)-H hydroxydifluoromethylation of imidazo[1,2-a]pyridines and afford a series of novel difluoromethylated carbinols in good to satisfactory yields with 29 examples. Furthermore, gram-scale and synthetic transformation experiments have also been achieved, demonstrating its potential applicable value in organic synthesis. This green protocol has several advantages, including being transition metal- and oxidant-free, being carried out at room temperature, having high efficiency, and having a wide substrate scope. Full article
(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications)
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Review

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25 pages, 7525 KiB  
Review
2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives
by Xiaofeng Zhang, Miao Liu, Weiqi Qiu and Wei Zhang
Molecules 2024, 29(6), 1241; https://doi.org/10.3390/molecules29061241 - 11 Mar 2024
Viewed by 760
Abstract
Quinoline is a privileged heterocyclic ring which can be found in many drug molecules and bioactive compounds. The development of synthetic methods for making quinoline derivatives continuously attracts the interest of organic and medicinal chemists. This paper highlights 2-azidobenzaldehyde-based [4+2] annulation for the [...] Read more.
Quinoline is a privileged heterocyclic ring which can be found in many drug molecules and bioactive compounds. The development of synthetic methods for making quinoline derivatives continuously attracts the interest of organic and medicinal chemists. This paper highlights 2-azidobenzaldehyde-based [4+2] annulation for the synthesis of quinoline derivatives including fused and spiro-quinolines, quinoline-4-ols, 4-aminoquinolines, and related compounds. Full article
(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications)
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