Special Issue "Heterocycle Reactions"

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: 31 December 2020.

Special Issue Editor

Prof. Dr. Fawaz Aldabbagh
Website
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 and Collections in MDPI journals

Special Issue Information

Dear Colleagues,

According to "Heterocyclic Chemistry" by J. A. Joule and K. Mills (Wiley, 5th Ed), "heterocyclic chemistry comprises at least half of all organic chemistry research worldwide". Many reactions proceed as predicted, while other reactions give unusual products, which perhaps do not fit the intended use but are nevertheless chemically interesting. Some reactions give more than one product, with selectivity tunable through optimization or biasing of reaction conditions. Often, interesting "side-products" are neglected in pursuit of a target compound.

This Special Issue welcomes the submission of any suitably fully characterized novel compound(s) from a given heterocyclic compound reaction. Please note that the reaction product does not necessarily have to be heterocyclic.

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 papers will be 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. Molbank is an international peer-reviewed open access quarterly 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 350 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

  • Heterocyclic chemistry
  • Aromatic heterocycles
  • Non-aromatic heterocycles
  • Fused heterocycles
  • Nitrogen
  • Oxygen
  • Sulfur
  • Radical
  • Spectroscopic properties
  • Halogenation
  • Organic chemistry
  • Medicinal chemistry

Published Papers (12 papers)

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Research

Open AccessFeature PaperShort Note
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol
Molbank 2020, 2020(2), M1140; https://doi.org/10.3390/M1140 - 03 Jun 2020
Abstract
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) [...] Read more.
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessCommunication
Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones
Molbank 2020, 2020(2), M1139; https://doi.org/10.3390/M1139 - 01 Jun 2020
Abstract
The reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-1,3-dimethylpiperazines (1 equiv), in THF, at ca. 20 °C gives (R) and (S)-3-chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones in 70% and 68% yields, respectively. The new compounds were fully characterized. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
Methyl 2-(1-methyl-3-oxoisoindolin-1-yl)acetate
Molbank 2020, 2020(2), M1131; https://doi.org/10.3390/M1131 - 08 May 2020
Abstract
In this work, we report a facile access to a 3,3-disubstituted isoindolinone by means of Krapcho decarboxylation reaction of the respective substituted dimethyl malonate derivative. Good isolated yields were obtained under mild reaction conditions. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessFeature PaperShort Note
2-(Fluoromethyl)-4,7-dimethoxy-1-methyl-1H-benzimidazole
Molbank 2020, 2020(2), M1129; https://doi.org/10.3390/M1129 - 01 May 2020
Abstract
Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) substitutes the TEMPO free radical with fluorine on 4,7-dimethoxy-1-methyl-2-{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-1H-benzimidazole to give the title compound in a 77% yield. A mechanism is proposed for the formation of this novel methylene fluoride. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessCommunication
Synthesis of (R) and (S)-3-Chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones
Molbank 2020, 2020(2), M1128; https://doi.org/10.3390/M1128 - 27 Apr 2020
Cited by 1
Abstract
Reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-3-methylmorpholines (2 equiv), in THF, at ca. 20 °C gave (R) and (S)-3-chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones in 95 and 97% yields, respectively. The new compounds were fully characterized. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessShort Note
2,6-exo-8,12-exo-10-Butyl-13-oxa-3,5-dithia-10-azatetracyclo[5.5.1.02,6.08,12]tridecane-9,11-dione
Molbank 2020, 2020(2), M1123; https://doi.org/10.3390/M1123 - 02 Apr 2020
Abstract
The title compound was obtained in low yield and spectroscopically characterised. Its X-ray structure was compared with the X-ray structures of other crystallographically-characterised 2-unsubstituted 1,3-dithiolanes. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessCommunication
6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation
Molbank 2020, 2020(1), M1118; https://doi.org/10.3390/M1118 - 05 Mar 2020
Abstract
The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
Diethyl pyrrole-2,5-dicarboxylate
Molbank 2020, 2020(1), M1117; https://doi.org/10.3390/M1117 - 17 Feb 2020
Abstract
The title compound was obtained in moderate yield by a new and unexpected base-induced ring contraction from a 1,4-thiazine precursor. Its X-ray structure showing hydrogen bonded dimers was compared with those of other crystallographically characterised 2-acylpyrroles. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessCommunication
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity
Molbank 2020, 2020(1), M1113; https://doi.org/10.3390/M1113 - 29 Jan 2020
Cited by 1
Abstract
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential [...] Read more.
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells). Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessCommunication
Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies
Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/M1085 - 14 Oct 2019
Cited by 1
Abstract
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS [...] Read more.
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessShort Note
3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione
Molbank 2019, 2019(4), M1083; https://doi.org/10.3390/M1083 - 03 Oct 2019
Abstract
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human [...] Read more.
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human blood cell. The title compound 5, subjected to in vitro activities, showed that it is cytotoxic with an IC50 of 42.30 µM and a good anti-inflammatory agent. The docking results against cyclin dependent kinase 2 (CDK2) (PDB ID: 3QQK) gave insights on its inhibitory activity. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole
Molbank 2019, 2019(3), M1074; https://doi.org/10.3390/M1074 - 19 Jul 2019
Abstract
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was [...] Read more.
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), MS data and elemental analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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