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Special Issue "Heteroatom Rich Organic Heterocycles"

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

Deadline for manuscript submissions: 31 December 2018

Special Issue Editors

Guest Editor
Prof. Dr. Panayiotis A. Koutentis

Department of Chemistry, University of Cyprus, P. O. Box 20537, 1678 Nicosia, Cyprus
Website | E-Mail
Phone: 0035722892783
Interests: heterocyclic chemistry; sulfur-nitrogen heterocycles; synthetic methods; azaacenes; zwitterionic acenes; stable organic radicals; biologically active heterocycles; isothiazoles; 1,2,3-dithiazoles; 1,2,6-thiadiazines;1,2,4-benzotriazines
Guest Editor
Dr. Andreas S. Kalogirou

Department of Pharmacy, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus
E-Mail

Special Issue Information

Dear Colleagues,

The International Union of Pure and Applied Chemistry (IUPAC) definition of a heterocycle requires a cyclic compound to contain at least two different elements as members of its ring(s). From the perspective of organic heterocycles, one of these elements must be carbon while the other is typically nitrogen, oxygen or sulfur. Common organic heterocycles contain either one or two heteroatoms, and many of these compounds have important commercial applications, as well as being important for many biological processes.

Less common heterocycles are those that contain either many heteroatoms, or a greater variety of heteroatoms. Increasing the atomic weight of the heteroatom also leads to less well known and less studied heterocycles. These heteroatom rich and often more complex heterocycles constitute an underexplored and underexploited area in the chemical sciences. The constant effort being made to increase structural diversity and to find new privileged structures in the biological and materials sciences can, therefore, only benefit from increased efforts to explore the area of rare heterocycles. This Special Issue encourages authors to report new developments in all aspects of heteroatom rich organic heterocycles, irrespective of ring size, that contain at least two different elements other than carbon and at least three heteroatoms within the heterocycles ring system.

Prof. Dr. Panayiotis A. Koutentis
Dr. Andreas S. Kalogirou
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 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
  • Selenium
  • Tin
  • Boron
  • Phosphorus
  • Silicon

Published Papers (6 papers)

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Research

Open AccessShort Note N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide
Molbank 2018, 2018(3), M1008; https://doi.org/10.3390/M1008
Received: 10 July 2018 / Revised: 24 July 2018 / Accepted: 24 July 2018 / Published: 25 July 2018
PDF Full-text (1123 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13
[...] Read more.
N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave insights on its plausible inhibitory action. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Figures

Graphical abstract

Open AccessShort Note 3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]
Molbank 2018, 2018(3), M1003; https://doi.org/10.3390/M1003
Received: 22 June 2018 / Revised: 2 July 2018 / Accepted: 3 July 2018 / Published: 5 July 2018
PDF Full-text (524 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved
[...] Read more.
The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved under the action of nitrating system HNO3/(CF3CO)2O in molar ratio 15:3 in CCl4 at −5 °C. The structure of 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was confirmed by means of 1H, 13C,14N-NMR, IR spectroscopy and high resolution mass spectra (HRMS). Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Figures

Graphical abstract

Open AccessFeature PaperCommunication 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
Molbank 2018, 2018(2), M997; https://doi.org/10.3390/M997
Received: 13 May 2018 / Revised: 15 May 2018 / Accepted: 16 May 2018 / Published: 16 May 2018
PDF Full-text (1191 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N
[...] Read more.
Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N′-(perfluorophenyl)benzohydrazide (3) (37%). The X-ray crystallography of 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) is provided. Microwave irradiation (100 W) of perfluorophenylbenzohydrazide 3 with K2CO3 (1.1 equiv) in THF at ca. 120 °C (sealed tube, 80 PSI) for 3 h gives oxadiazine 5 (85%), while reduction of the nitro group using Sn (4 equiv) in glacial acetic acid at ca. 20 °C for 30 min, followed by cyclodehydration at ca. 118 °C for 20 min and treatment with 2 M NaOH for 24 h resulted in 1-(perfluorophenyl)-3-phenyl-1,2,4-benzotriazin-4-yl (4) with 93% yield. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
Molbank 2018, 2018(2), M993; https://doi.org/10.3390/M993
Received: 28 March 2018 / Revised: 25 April 2018 / Accepted: 26 April 2018 / Published: 27 April 2018
PDF Full-text (745 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism
[...] Read more.
A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism is proposed for its formation. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Figures

Graphical abstract

Open AccessFeature PaperShort Note 5,5′-Bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione
Molbank 2018, 2018(1), M987; https://doi.org/10.3390/M987
Received: 23 February 2018 / Revised: 1 March 2018 / Accepted: 6 March 2018 / Published: 8 March 2018
PDF Full-text (567 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Stille coupling of 5,5′-dichloro-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione (8) with 9-decyl-3-[5-(tributylstannyl)thien-2-yl]-9H-carbazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110 °C, for 2 h, gave 5,5′-bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione (7) in 51% yield. The latter is investigated as an oligomer donor for organic photovoltaics. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessShort Note 4,7-Dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide
Molbank 2018, 2018(1), M982; https://doi.org/10.3390/M982
Received: 2 February 2018 / Revised: 15 February 2018 / Accepted: 16 February 2018 / Published: 18 February 2018
PDF Full-text (359 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Dihalogenated derivatives of [1,2,5]chalcogenadiazolo[3,4-d]pyridazines are of interest as precursors for both photovoltaic materials and biologically active compounds. In this communication, 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide was prepared via the reaction of 3,6-dichloro-5-nitropyridazin-4-amine with oxidizing agents; the best yield of the target compound
[...] Read more.
Dihalogenated derivatives of [1,2,5]chalcogenadiazolo[3,4-d]pyridazines are of interest as precursors for both photovoltaic materials and biologically active compounds. In this communication, 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide was prepared via the reaction of 3,6-dichloro-5-nitropyridazin-4-amine with oxidizing agents; the best yield of the target compound was achieved in the reaction with (diacetoxyiodo)benzene in benzene by heating at reflux for two hours. The structure of the newly synthesized compound was established by means of 13C-NMR and IR spectroscopy, mass-spectrometry and elemental analysis. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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