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Heterocyclic Chemistry with Applications
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Special Issue "Heterocyclic Chemistry with Applications"

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

Deadline for manuscript submissions: 1 November 2023 | Viewed by 2746

Special Issue Editor

Prof. Dr. Fawaz Aldabbagh

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Guest Editor
Department of Pharmacy, School of Life Sciences, Pharmacy & Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames KT1 2EE, UK
Interests: free radical organic and polymer chemistry; heterocyclic and medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is dedicated to the broad range of applications of heterocycles, including in materials science and medicine. Recently famed applications include those in synthesis, with the Nobel Prize in Chemistry 2021 being jointly awarded to Benjamin List and David W.C. MacMillan for the development of asymmetric organocatalysis. Heterocycles are usually five or six-membered rings that are either fused or not fused onto other rings and that most often contain nitrogen atom(s) and/or oxygen atom(s). Many heterocycles have found applications as stable free radicals or as highly conjugated molecules in the photoredox catalysis of soft visible light-mediated reactions. I am therefore looking forward to receiving timeless research articles, communications, and reviews detailing the latest advances in heterocyclic chemistry with applications in medicinal, polymer, and synthetic chemistry, among others.

This Special Issue is running in parallel with another Special Issue called “Heterocycle Reaction” in our sister journal, Molbank: https://www.mdpi.com/journal/molbank/special_issues/Heterocycle_Reaction

Prof. Dr. Fawaz Aldabbagh
Guest Editor

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 2300 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

  • heterocycles
  • medicinal chemistry
  • natural products
  • organic synthesis
  • radicals
  • reactive intermediates
  • synthetic methods

Published Papers (3 papers)

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Article
Regioselective Cyclic Iminium Formation of Ugi Advanced Intermediates: Rapid Access to 3,4-Dihydropyrazin-2(1H)-ones and Other Diverse Nitrogen-Containing Heterocycles
by
Naděžda Cankařová
and
Viktor Krchňák
Molecules 2023, 28(7), 3062; https://doi.org/10.3390/molecules28073062 - 29 Mar 2023
Viewed by 442
Abstract
Herein, advanced intermediates were synthesized through Ugi four-component reactions of isocyanides, aldehydes, masked amino aldehyde, and carboxylic acids, including N-protected amino acids. The presence of a masked aldehyde enabled acid-mediated deprotection and subsequent cyclization via the carbonyl carbon and the amide nitrogen. [...] Read more.
Herein, advanced intermediates were synthesized through Ugi four-component reactions of isocyanides, aldehydes, masked amino aldehyde, and carboxylic acids, including N-protected amino acids. The presence of a masked aldehyde enabled acid-mediated deprotection and subsequent cyclization via the carbonyl carbon and the amide nitrogen. Utilizing N-protected amino acid as a carboxylic acid component, Ugi intermediates could be cyclized from two possible directions to target 3,4-dihydropyrazin-2(1H)-ones. Cyclization to the amino terminus (westbound) and to the carboxyl terminus (eastbound) was demonstrated. Deliberate selection of building blocks drove the reaction regioselectively and yielded diverse heterocycles containing a 3,4-dihydropyrazin-2(1H)-one core, pyrazin-2(1H)-one, and piperazin-2-one, as well as a tricyclic framework with a 3D architecture, 2,3-dihydro-2,6-methanobenzo[h][1,3,6]triazonine-4,7(1H,5H)-dione, from Ugi adducts under mild reaction conditions. The latter bridged heterocycle was achieved diastereoselectively. The reported chemistry represents diversity-oriented synthesis. One common Ugi advanced intermediate was, without isolation, rapidly transformed into various nitrogen-containing heterocycles. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry with Applications)
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Article
Pyrimidines-Based Heterocyclic Compounds: Synthesis, Cytoxicity Evaluation and Molecular Docking
by
Mohamed A. El-Atawy
,
Najla A. Alshaye
,
Nada Elrubi
,
Ezzat A. Hamed
and
Alaa Z. Omar
Molecules 2022, 27(15), 4912; https://doi.org/10.3390/molecules27154912 - 01 Aug 2022
Cited by 1 | Viewed by 1037
Abstract
A variety of structurally different pyrimidines were synthesized. Elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy were used to confirm the chemical structures of all prepared compounds. The synthesized pyrimidines were screened against the growth of five human cancer cell [...] Read more.
A variety of structurally different pyrimidines were synthesized. Elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy were used to confirm the chemical structures of all prepared compounds. The synthesized pyrimidines were screened against the growth of five human cancer cell lines (prostate carcinoma PC3, liver carcinoma HepG-2, human colon cancer HCT-116, human breast cancer MCF-7, human lung cancer A-549), and normal human lung fibroblasts (MRC-5) using MTT assay. Most of the screened pyrimidines have anti-proliferative activity on the growth of the PC3 cell line. Compounds 3b and 3d were more potent than the reference vinblastine sulfate (~2 to 3 × fold) and they can be considered promising leads for treating prostate cancer disease. Moreover, the screened compounds 3b, 3f, 3g, 3h, and 5 were assessed according to the values of their selectivity index (SI) and were found to be more selective and safer than vinblastine sulfate. Furthermore, using in silico computational tools, the physicochemical properties of all pyrimidine ligands were assessed, and the synthesized compounds fall within the criteria of RO5, thus having the potential to be orally bioavailable. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry with Applications)
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Article
Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
by
Kaikai Wang
,
Yanli Li
,
Wei Zhang
,
Rongxiang Chen
,
Xueji Ma
,
Mingyue Wang
and
Nan Zhou
Molecules 2022, 27(10), 3064; https://doi.org/10.3390/molecules27103064 - 10 May 2022
Viewed by 797
Abstract
A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, [...] Read more.
A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry with Applications)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Quinoxalin-2(1H)-ones: Electrochemical and Photochemical Functionalization, biological activity and Applications
Authors: Shi-Hui Shi, Runmei Li, Hao-Yu Li, Rui Tian
Affiliation: Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan’an University, Yan’an 716000, Shaanxi, China
Abstract: Quinoxalin-2(1H)-ones is a versatile heterocyclic moiety that has been frequently found in a variety of pharmacologically active compounds with biological or pharmaceutical applications. Therefore, the functionalization of quinoxalin-2(1H)-ones has attracted extensive attention. But the conventional chemical method has largely involved the use of expensive and toxic catalysts as well as the use of stoichiometric and perhaps dangerous reagents, compromising the overall sustainable nature. In this respect, electrochemical and photochemical has been identified as a sustainable and scalable strategy that exploits electron and photon in place of byproduct-generating chemical reagents. This review provides an overview on the most recent and significant achievements, in electro- and photochemically functionalized quinoxalin-2(1H)-ones with an emphasis on both synthetic outcomes and reaction mechanisms, and showcases the innate advantages and exciting potentials of electrochemical and photochemical organic synthesis.

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