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 March 2021.

Special Issue Editors

Prof. Dr. Panayiotis A. Koutentis
Website
Guest Editor
Department of Chemistry, University of Cyprus, P. O. Box 20537, 1678 Nicosia, Cyprus
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
Special Issues and Collections in MDPI journals
Dr. Andreas S. Kalogirou

Guest Editor
Department of Life Sciences, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus
Special Issues and Collections in MDPI journals

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

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Keywords

  • Heterocyclic Chemistry
  • Aromatic Heterocycles
  • Non-aromatic Heterocycles
  • Fused Heterocycles
  • Nitrogen
  • Oxygen
  • Sulfur
  • Selenium
  • Tin
  • Boron
  • Phosphorus
  • Silicon

Published Papers (11 papers)

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Research

Open AccessShort Note
5,5′-Thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one)
Molbank 2019, 2019(2), M1064; https://doi.org/10.3390/M1064 - 09 Jun 2019
Abstract
The reaction of 3-chloro-5-methoxy-4H-1,2,6-thiadiazin-4-one (9) with Na2S·9H2O (0.5 equiv) in tetrahydrofuran (THF) at ca. 20 °C for 20 h gives 5,5′-thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one) (10) in a 44% yield as yellow needles. The compound was fully characterized. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note
3,5-Bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one
Molbank 2019, 2019(1), M1045; https://doi.org/10.3390/M1045 - 15 Jan 2019
Abstract
Stille coupling of 3,5-bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-one (10) with 2-(tri-n-butylstannyl)thiazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110 °C, for 2 h, gave 3,5-bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one (9) in 81% yield. The latter is evaluated for its electronic properties. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note
3-Chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one
Molbank 2019, 2019(1), M1043; https://doi.org/10.3390/M1043 - 09 Jan 2019
Abstract
Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph3P)2Cl2 in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. [...] Read more.
Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph3P)2Cl2 in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. The latter is a potentially useful building block for the synthesis of oligomeric and polymeric donors for organic photovoltaics. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note
5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide
Molbank 2018, 2018(3), M1018; https://doi.org/10.3390/M1018 - 11 Sep 2018
Abstract
In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N [...] Read more.
In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N′-chlorosulfonyl chloroformamidine. The product structure, confirmed by X-ray crystallography, bears an exocyclic NH2 group, which should enable synthesis of an extended range of derivatives of this unusual scaffold. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine
Molbank 2018, 2018(3), M1014; https://doi.org/10.3390/M1014 - 24 Aug 2018
Abstract
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound [...] Read more.
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound was spectroscopically characterized by UV-Vis, FTIR, DSC, 13C/1H-NMR, and sass spectrometric techniques. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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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 - 25 Jul 2018
Cited by 1
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)
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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 - 05 Jul 2018
Cited by 4
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)
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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 - 16 May 2018
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 - 27 Apr 2018
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)
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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 - 08 Mar 2018
Cited by 2
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 - 18 Feb 2018
Cited by 1
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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