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Molbank
Special Issues
Heteroatom Rich Organic Heterocycles
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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: closed (31 May 2022) | Viewed by 50502

Special Issue Editors

Prof. Dr. Panayiotis A. Koutentis

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Guest Editor
Department of Chemistry, University of Cyprus, P. O. Box 20537, Nicosia 1678, 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, Collections and Topics in MDPI journals
Dr. Andreas S. Kalogirou

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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, Collections and Topics 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 (22 papers)

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Research

6 pages, 821 KiB  
Short Note
3-Phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine
by Alia D. Aouant and George Varvounis
Molbank 2022, 2022(3), M1432; https://0-doi-org.brum.beds.ac.uk/10.3390/M1432 - 24 Aug 2022
Viewed by 1546
Abstract
In this study, we considered the reaction of (E)-1-[(2-phenylhydrazono)methyl]naphthalen-2-ol with iodobenzene diacetate in dichloromethane-produced novel 3-phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine in 11% yield. By analogy to previously published work, we suggested that the reaction proceeds via the intermediacy of an o [...] Read more.
In this study, we considered the reaction of (E)-1-[(2-phenylhydrazono)methyl]naphthalen-2-ol with iodobenzene diacetate in dichloromethane-produced novel 3-phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine in 11% yield. By analogy to previously published work, we suggested that the reaction proceeds via the intermediacy of an o-naphthoquinone azomethide that undergoes conjugated 6π-electrocylization to produce the product. 1D, 2D NMR, HRMS, IR, and UV-VIS spectra provided information that supported the structure of the product. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

4 pages, 374 KiB  
Short Note
4-Amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-Oxide
by Margarita A. Epishina, Alexander S. Kulikov and Leonid L. Fershtat
Molbank 2022, 2022(3), M1425; https://0-doi-org.brum.beds.ac.uk/10.3390/M1425 - 12 Aug 2022
Viewed by 1611
Abstract
Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans [...] Read more.
Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans have remained unknown so far. In this communication, a simple method for the synthesis of 4-amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-oxide is described. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR and IR spectroscopy. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

4 pages, 399 KiB  
Short Note
(E)-7-(4-(Diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile
by Timofey N. Chmovzh, Timofey A. Kudryashev and Oleg A. Rakitin
Molbank 2022, 2022(2), M1385; https://0-doi-org.brum.beds.ac.uk/10.3390/M1385 - 15 Jun 2022
Cited by 1 | Viewed by 1320
Abstract
Donor-acceptor-donor (D-A-A) structures with 2,1,3-benzothiadiazole as an internal acceptor and the 4(7)-cyanogroup as anchor acceptor have been investigated for various photovoltaic applications such as dye-sensitized solar cells (DSSCs) and organic light emitting diodes (OLEDs). They are usually obtained by cyanation of 4(7)-bromo-2,1,3-benzothiadiazoles. In [...] Read more.
Donor-acceptor-donor (D-A-A) structures with 2,1,3-benzothiadiazole as an internal acceptor and the 4(7)-cyanogroup as anchor acceptor have been investigated for various photovoltaic applications such as dye-sensitized solar cells (DSSCs) and organic light emitting diodes (OLEDs). They are usually obtained by cyanation of 4(7)-bromo-2,1,3-benzothiadiazoles. In this communication, the reaction of (E)-4-(2-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)vinyl)-N,N-diphenylaniline with cyanating agents was studied and it was shown that the best yield of (E)-7-(4-(diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile was achieved by heating with zinc cyanide in NMP at 120 °C in the presence of tetrakis(triphenylphosphine)palladium (0). The structure of newly synthesized compound was established by means of an elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, IR, UV spectroscopy and mass-spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

3 pages, 392 KiB  
Short Note
5,5′-Thiobis(4-chloro-3H-1,2-dithiole-3-thione)
by Vladimir A. Ogurtsov and Oleg A. Rakitin
Molbank 2022, 2022(2), M1371; https://0-doi-org.brum.beds.ac.uk/10.3390/M1371 - 27 May 2022
Cited by 1 | Viewed by 1235
Abstract
3H-1,2-Dithiole-3-thiones are important compounds with many types of significant pharmacological activity. Although many derivatives of this class have been described in the literature, their thioethers have not previously been obtained. In this communication, it is shown that the reaction of 4,5-dichloro-3 [...] Read more.
3H-1,2-Dithiole-3-thiones are important compounds with many types of significant pharmacological activity. Although many derivatives of this class have been described in the literature, their thioethers have not previously been obtained. In this communication, it is shown that the reaction of 4,5-dichloro-3H-1,2-dithiole-3-thione with potassium isocyanate unexpectedly gave 5,5′-thiobis(4-chloro-3H-1,2-dithiole-3-thione). The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 13C NMR and IR spectroscopy, and mass spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

4 pages, 411 KiB  
Short Note
(E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline
by Timofey N. Chmovzh and Oleg A. Rakitin
Molbank 2022, 2022(2), M1368; https://0-doi-org.brum.beds.ac.uk/10.3390/M1368 - 19 May 2022
Cited by 1 | Viewed by 1456
Abstract
(Diphenylamino)phenylethenyl group-containing chromophores are widely employed to design effective materials with useful electronic properties. In this communication, (E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline was regioselectively obtained by the Heck reaction of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine with N,N-diphenyl-4-vinylaniline. The [...] Read more.
(Diphenylamino)phenylethenyl group-containing chromophores are widely employed to design effective materials with useful electronic properties. In this communication, (E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline was regioselectively obtained by the Heck reaction of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine with N,N-diphenyl-4-vinylaniline. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C, NOESY NMR, IR and UV spectroscopy and mass-spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Figure 1

4 pages, 632 KiB  
Short Note
4-Bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)
by Timofey N. Chmovzh, Daria A. Alekhina, Timofey A. Kudryashev and Oleg A. Rakitin
Molbank 2022, 2022(2), M1362; https://0-doi-org.brum.beds.ac.uk/10.3390/M1362 - 12 May 2022
Cited by 4 | Viewed by 2447
Abstract
Bromoderivatives of benzofused 1,2,5-thiadiazoles are important precursors for the synthesis of dyes, which are widely used to design effective photovoltaic materials. In this study, 4-bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole was selectively obtained from the bromination of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole. The structure [...] Read more.
Bromoderivatives of benzofused 1,2,5-thiadiazoles are important precursors for the synthesis of dyes, which are widely used to design effective photovoltaic materials. In this study, 4-bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole was selectively obtained from the bromination of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H-, 13C-NMR, IR and UV spectroscopy and mass spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

5 pages, 366 KiB  
Short Note
4,7-Bis(5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine
by Timofey N. Chmovzh, Vladislav M. Korshunov, Ilya V. Taydakov and Oleg A. Rakitin
Molbank 2022, 2022(1), M1332; https://0-doi-org.brum.beds.ac.uk/10.3390/M1332 - 08 Feb 2022
Viewed by 1957
Abstract
Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized [...] Read more.
Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized compounds was established by high resolution mass-spectrometry, 1H, 13C NMR, IR, and UV spectroscopy and mass-spectrometry. A study of the luminescent properties of the dye showed that it exhibits fluorescence in the near infrared region of the spectrum, which makes it a promising compound for use as an active emitting layer in NIR OLED as well as for other possible applications as an IR luminophore. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

4 pages, 347 KiB  
Short Note
4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine
by Timofey N. Chmovzh, Timofey A. Kudryashev and Oleg A. Rakitin
Molbank 2021, 2021(4), M1291; https://0-doi-org.brum.beds.ac.uk/10.3390/M1291 - 25 Oct 2021
Cited by 2 | Viewed by 2188
Abstract
Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic [...] Read more.
Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic nucleophilic substitution SNAr and Buchwald–Hartwig cross-coupling. The structure of the newly synthesized compounds was established by means of elemental analysis; high-resolution mass spectrometry; 1H, 13C NMR, IR and UV spectroscopy; and mass spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

4 pages, 332 KiB  
Short Note
7-Bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one
by Timofey N. Chmovzh and Oleg A. Rakitin
Molbank 2021, 2021(2), M1229; https://0-doi-org.brum.beds.ac.uk/10.3390/M1229 - 05 Jun 2021
Cited by 1 | Viewed by 1875
Abstract
New heterocyclic systems containing 1,2,5-chalcogenadiazoles are of great interest for the creation of organic photovoltaic materials and biologically active compounds. In this communication, 3,6-dibromopyridazine-4,5-diamine was investigated in reaction with selenium dioxide in order to obtain 4,7-dibromo-[1,2,5]selenadiazolo[3,4-d]pyridazine. We found that 7-bromo-[1,2,5]selenadiazolo[3,4-d [...] Read more.
New heterocyclic systems containing 1,2,5-chalcogenadiazoles are of great interest for the creation of organic photovoltaic materials and biologically active compounds. In this communication, 3,6-dibromopyridazine-4,5-diamine was investigated in reaction with selenium dioxide in order to obtain 4,7-dibromo-[1,2,5]selenadiazolo[3,4-d]pyridazine. We found that 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one, the first representative of the new heterocyclic system, was isolated as a hydrolysis product of the corresponding 4,7-dibromoderivative. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy, and mass spectrometry. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

6 pages, 1155 KiB  
Short Note
Methyl 2-Amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate
by Karolina Dzedulionytė, Paulina Voznikaitė, Aurimas Bieliauskas, Vida Malinauskienė, Frank A. Sløk and Algirdas Šačkus
Molbank 2021, 2021(2), M1207; https://0-doi-org.brum.beds.ac.uk/10.3390/M1207 - 01 May 2021
Cited by 3 | Viewed by 2233
Abstract
Methyl 2-amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate as a newly functionalized heterocyclic amino acid was obtained via [3+2] cycloaddition. The structure of the novel 1,3-selenazole was unequivocally confirmed by detailed 1H, 13C, 15N, and 77Se NMR spectroscopic experiments, HRMS and elemental analysis. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Figure 1

5 pages, 481 KiB  
Short Note
4-(7-Bromobenzo[d][1,2,3]thiadiazol-4-yl)morpholine
by Nikita S. Gudim, Ekaterina A. Knyazeva, Natalia V. Obruchnikova, Oleg A. Rakitin and Vadim V. Popov
Molbank 2021, 2021(2), M1202; https://0-doi-org.brum.beds.ac.uk/10.3390/M1202 - 13 Apr 2021
Cited by 3 | Viewed by 2058
Abstract
Dibromoderivatives of benzofused chalcogen-nitrogen heterocycles are important precursors in the synthesis of various photovoltaic materials. 4,7-Dibromobenzo[d][1,2,3]thiadiazole is a practically unexplored compound in this series. In this communication, it was shown that the nucleophilic substitution of 4,7-dibromobenzo[d][1,2,3]thiadiazole with morpholine gave [...] Read more.
Dibromoderivatives of benzofused chalcogen-nitrogen heterocycles are important precursors in the synthesis of various photovoltaic materials. 4,7-Dibromobenzo[d][1,2,3]thiadiazole is a practically unexplored compound in this series. In this communication, it was shown that the nucleophilic substitution of 4,7-dibromobenzo[d][1,2,3]thiadiazole with morpholine gave selectively 4-substituted product—4-(7-bromobenzo[d][1,2,3]thiadiazol-4-yl)morpholine. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Figure 1

4 pages, 712 KiB  
Short Note
5,5′-Thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one)
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2019, 2019(2), M1064; https://0-doi-org.brum.beds.ac.uk/10.3390/M1064 - 09 Jun 2019
Viewed by 1803
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)
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Figure 1

5 pages, 700 KiB  
Short Note
3,5-Bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2019, 2019(1), M1045; https://0-doi-org.brum.beds.ac.uk/10.3390/M1045 - 15 Jan 2019
Viewed by 2127
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)
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Figure 1

5 pages, 691 KiB  
Short Note
3-Chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2019, 2019(1), M1043; https://0-doi-org.brum.beds.ac.uk/10.3390/M1043 - 09 Jan 2019
Viewed by 2066
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)
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Figure 1

6 pages, 1146 KiB  
Short Note
5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide
by Victor Tran, Craig M. Forsyth and Craig L. Francis
Molbank 2018, 2018(3), M1018; https://0-doi-org.brum.beds.ac.uk/10.3390/M1018 - 11 Sep 2018
Viewed by 2566
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)
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Figure 1

5 pages, 358 KiB  
Short Note
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine
by Ganesh Shimoga, Eun-Jae Shin and Sang-Youn Kim
Molbank 2018, 2018(3), M1014; https://0-doi-org.brum.beds.ac.uk/10.3390/M1014 - 24 Aug 2018
Viewed by 3063
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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Graphical abstract

5 pages, 1123 KiB  
Short Note
N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide
by Nikil Purushotham and Boja Poojary
Molbank 2018, 2018(3), M1008; https://0-doi-org.brum.beds.ac.uk/10.3390/M1008 - 25 Jul 2018
Cited by 1 | Viewed by 2806
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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4 pages, 524 KiB  
Short Note
3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]
by Alexander Larin, Igor Ovchinnikov, Leonid Fershtat and Nina Makhova
Molbank 2018, 2018(3), M1003; https://0-doi-org.brum.beds.ac.uk/10.3390/M1003 - 05 Jul 2018
Cited by 5 | Viewed by 2873
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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8 pages, 1191 KiB  
Communication
5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
by Georgia A. Zissimou, Andreas Kourtellaris and Panayiotis A. Koutentis
Molbank 2018, 2018(2), M997; https://0-doi-org.brum.beds.ac.uk/10.3390/M997 - 16 May 2018
Viewed by 2597
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)
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5 pages, 745 KiB  
Short Note
Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
by R. Alan Aitken and Karamat Ali
Molbank 2018, 2018(2), M993; https://0-doi-org.brum.beds.ac.uk/10.3390/M993 - 27 Apr 2018
Cited by 1 | Viewed by 2688
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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Graphical abstract

5 pages, 567 KiB  
Short 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
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2018, 2018(1), M987; https://0-doi-org.brum.beds.ac.uk/10.3390/M987 - 08 Mar 2018
Cited by 2 | Viewed by 2798
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)
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Figure 1

3 pages, 359 KiB  
Short Note
4,7-Dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide
by Timofey Chmovzh, Ekaterina Knyazeva, Vadim Popov and Oleg Rakitin
Molbank 2018, 2018(1), M982; https://0-doi-org.brum.beds.ac.uk/10.3390/M982 - 18 Feb 2018
Cited by 4 | Viewed by 3381
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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