Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Heterocyclic Communications

Editor-in-Chief: Strekowski, Lucjan

Ed. by Baumstark, Alfons L. / Saczewski, Jaroslaw / Stephens, Chad / Yamada, Hidetoshi

6 Issues per year


IMPACT FACTOR 2017: 0.700

CiteScore 2017: 0.66

SCImago Journal Rank (SJR) 2017: 0.199
Source Normalized Impact per Paper (SNIP) 2017: 0.263

Online
ISSN
2191-0197
See all formats and pricing
More options …
Volume 22, Issue 6

Issues

Heterocyclization of 5,6-disubstituted 3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-one with p-alkoxyphenyltellurium trichloride

Mykola Kut / Mikhajlo Onysko / Vasyl Lendel
Published Online: 2016-11-28 | DOI: https://doi.org/10.1515/hc-2016-0169

Abstract

Electrophilic heterocyclization of 5,6-disubstituted 3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-ones by treatment with p-alkoxyphenyltellurium trichlorides leads to annulation of the thiazoline moiety with the formation of 6,7-disubstituted-2-[dichloro-(p-alkoxyphenyl)telluromethyl]-2,3-dihydro-5Н-[1,3]thiazolo[3,2-а]thieno[2,3-d]pyrimidin-5-one hydrochlorides.

Keywords: 3-alkenyl-2-thioxothieno[2,3-d]pyrimidine-4-one; [1,3]thiazolo[3,2-а]thieno[2,3-d]pyrimidin-5-one; electrophilic cyclization; p-alkoxyphenyltellurium trichloride; regioselectivity

References

  • [1]

    Cunha, R. L. O. R.; Urano, M. E.; Chagas, J. R.; Almeida, P. C.; Bincoletto, C.; Tersariolb, I. L. S.; Comasseto, J. V. Tellurium-based cysteine protease inhibitors: evaluation of novel organotellurium(IV) compounds as inhibitors of human cathepsin B. Bioorg. Med. Chem. Lett. 2005, 15, 755–760.Google Scholar

  • [2]

    Abondanza, T. S.; Oliveira, C. R.; Barbosa C. M. V.; Pereira, F. E. G.; Cunha R. L. O. R.; Caires, A. C. F.; Comasseto, J. V.; Queiroz, M. L. S.; Valadares, M. C.; Bincoletto, C. Bcl-2 expression and apoptosis induction in human HL-60 leukaemic cells treated with a novel organotellurium(IV) compound RT-04. Food Chem. Toxicol. 2008, 46, 2540–2445.Web of ScienceGoogle Scholar

  • [3]

    Cunha R. L. O. R.; Gouvea, I. E.; Juliano, L. A glimpse on biological activities of tellurium compounds. Ann. Braz. Acad. Sci. 2009, 81, 393–407.Google Scholar

  • [4]

    Andersson, C.; Brattsand, R.; Hallberg, A.; Engman, L.; Persson, J.; Moldeus, P.; Cotgreave, I. Diaryl tellurides as inhibitors of lipid peroxidation in biological and chemical systems. Free Radical Res. 1994, 20, 401–410.Google Scholar

  • [5]

    Soni, D.; Gupta, P.; Kumar, Y.; Chandrashekhar, T. Antibacterial activity of some unsymmetrical diorganyltellurium(IV) dichlorides. Indian J. Biochem. Biophys. 2005, 42, 398–340.Google Scholar

  • [6]

    Goodrum, J. F. Role of organotellurium compounds in neuropathy. Neurochem. Res. 1998, 3, 1313–1319.Google Scholar

  • [7]

    Laden, B.; Porter, T. Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. J. Lipid Res. 2001, 42, 235–240.Google Scholar

  • [8]

    Wagner, R.; Toews, A.; Morell, P. Tellurium blocks cholesterol synthesis by inhibiting squalene metabolism: preferential vulnerability to this metabolic block leads to peripheral nervous system demyelination. J Neurochem. 1991, 57, 1891–1901.Google Scholar

  • [9]

    Wagner, R.; Toews, A.; Morell, P. Tellurite specifically affects squalene epoxidase investigations examining the mechanism of telluriuminduced neuropathy. J. Neurochem. 1995, 64, 2169–2176.Google Scholar

  • [10]

    Wieslander, E.; Engman, L.; Svensjö, E.; Erlansson, M.; Johansson, U.; Linden, M.; Andersson, C.; Brattsand, R. Antioxidative properties of organotellurium compounds in cell systems. Biochem. Pharmacol. 1998, 55, 573–584.Google Scholar

  • [11]

    Brodsky, M.; Yosef, S.; Galit, R.; Albeck, M.; Longo, D.; Albeck, A.; Sredni, B. The synthetic tellurium compound, AS101, is a novel inhibitor of IL-1β converting enzyme. J. Interferon Cytokine Res. 2007, 27, 453–462.Google Scholar

  • [12]

    Onysko, M.; Lendel, V.; Stanynets, V. Interaction 2 propargylthio-3-phenyl-4-oxo-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine with selenium and tellurium tetrahalides. Ukr. Chem. J. 1999, 65, 116–118.Google Scholar

  • [13]

    Slivka, M.; Korol, N.; Rusyn, I.; Lendel, V. Synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts via regioselective electrophilic cyclization of 3-s-alkenylthio-4H-1,2,4-triazoles. Heterocycl. Cоmmun. 2015, 21, 397–401.Google Scholar

  • [14]

    Sadekov, I.; Minkin, V. Tellurium-nitrogen-containing heterocycles. Adv. Heterocycl. Chem. 2001, 79, 2–36.Google Scholar

  • [15]

    Comasseto, J.; Grazini, M. Cyclization of olefinic benzyl ethers with aryltellurium trichlorides. Synth. Commun. 1992, 22, 949–954.Google Scholar

  • [16]

    Borecka, B.; Cameron, S.; Malik, A.; Smith, B. Stereospecific reactions of aryltellurium(lV) trichlorides with 3-cyclohexene-1 –methanol and 3-cyclohexene-1,1-dimethanol: the X-ray crystal structure of 2',4'-dimethoxyphenyl(trans-6-moxabicyclo[3.2.1]oct-4-yl)tellurium(IV) dichloride. Can. J. Chem. 1995, 73, 255–263.Google Scholar

  • [17]

    Comasseto, J.; Petragnani, N. Cyclofunctionalization with aryltellurium trichlorides. Synth. Commun. 1983, 13, 889–900.Google Scholar

  • [18]

    Princival, C.; Dos Santos, A.; Comasseto, J. Solventless and mild procedure to prepare organotellurium(IV) compounds under microwave irradiation. J. Braz. Chem. Soc. 2015, 26, 832–836.Google Scholar

  • [19]

    Reichel, L.; Kirschbaum, E. Über aromatische Tellurverbindungen. (I. Mitteilung über Organometallverbindungen). Ann. Chem. 1936, 523, 211–223.Google Scholar

  • [20]

    Fizer, M. Methallyl isothiocyanate. Synlett 2013; 24, 2019–2020.CrossrefWeb of ScienceGoogle Scholar

  • [21]

    Smolanka, I. V.; Dobosh, A. A.; Khripak, S. M. Halogenation of some substituted 3-allyl-2-mercapto-3,4-dihydrothieno [2,3-d]pyrimidines. Chem. Heterocycl. Compd. 1973, 9, 1169–1170Google Scholar

  • [22]

    Sauter, F.; Deinhammer, W. Synthese von 2-Mercapto-thieno[2,3-d]pyrimidin-4(3H)-on-Derivaten. Monatsh. Chem. 1973, 104, 1593–1598.Google Scholar

About the article

Received: 2016-10-05

Accepted: 2016-10-31

Published Online: 2016-11-28

Published in Print: 2016-12-01


Citation Information: Heterocyclic Communications, Volume 22, Issue 6, Pages 347–350, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: https://doi.org/10.1515/hc-2016-0169.

Export Citation

©2016 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Mykola Kut, Maksym Fizer, Mikhajlo Onysko, and Vasil Lendel
Journal of Heterocyclic Chemistry, 2018

Comments (0)

Please log in or register to comment.
Log in