Skip to main content

Advertisement

Log in

Microwave synthesis of 2-[(E)-2-(1H-indol-3-yl)vinyl]hetarenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A new highly efficient method for the condensation of (indol-3-yl)carbaldehydes with 2-methylazoles and 2-methylazines under activation with microwave irradiation is developed. The method provides high yields of structural scaffolds of bishetarylethylene fluorescent sensors that found widespread application in medicinal, bioorganic, and pharmaceutical chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Figure 1

Similar content being viewed by others

References

  1. (a) MacLaren, D. C.; Toyokuni, T.; Cherry, S. R.; Barrio, J. R.; Phelps, M. E.; Herschman, H. R.; Gambhir, S. S. Biol. Psychiatr. 2000, 48, 337. (b) Bartlett, D. W.; Su, H.; Hildebrandt, I. J.; Weber, W. A.; Davis, M. E. Proc. Natl. Acad. Sci. 2007, 104, 15549. (c) Tian, X.; Aruva, M. R.; Zhang, K.; Shanthly, N.; Cardi, C. A.; Thakur, M. L.; Wickstrom, E. J. Nucl. Med. 2007, 48, 1699. (d) Cherry, S. R. J. Nucl. Med. 2006, 47, 1735. (e) de Vries, E. F. J.; Vroegh, J.; Dijkstra, G.; Moshage, H.; Elsinga, P. H.; Jansen, P. L. M.; Vaalburg, W. Nucl. Med. Biol. 2004, 31, 605. (f) Perera, R. J.; Ray, A. BioDrugs 2007, 21, 97.

  2. Wang, M.; Gao, M.; Miller, K. D.; Sledge, G. W; Hutchins, G. D.; Zheng, Q.-H. Eur. J. Med. Chem. 2009, 44, 2300.

    Article  CAS  Google Scholar 

  3. Li, Q. Chang, Y.-T. Nat. Protoc. 2006, 1, 2922.

    Article  CAS  Google Scholar 

  4. (a) Ballou, B.; Fisher, G.W.; Deng, J. S.; Hakala, T. R.; Srivastava, M.; Farkas, D. L. Cancer Detect. Prev. 1998, 22, 251. (b) Bogdanov, A. A., Jr.; Lin, C. P.; Simonova, M.; Matuszewski, L.; Weissleder, R. Neoplasia 2002, 4, 228.

  5. Li, Q.; Kim, Y.; Namm, J.; Kulkarni, A.; Rosania, G. R.; Ahn, Y.-H.; Chang, Y.-T. Chem. Biol. 2006, 13, 615.

    Article  CAS  Google Scholar 

  6. (a) Bohländer, P. R.; Vilaivan, T.; Wagenknecht, H. A. Org. Biomol. Chem. 2015, 13, 9223. (b) Bohländer, P. R.; Wagenknecht, H.-A. Org. Biomol. Chem. 2013, 11, 7458.

  7. Barresi, V.; Bonaccorso, C.; Consiglio, G.; Goracci, L.; Musso, N.; Musumarra, G.; Satriano, C.; Fortuna, C. G. Mol. BioSystems 2013, 9, 2426.

    Article  CAS  Google Scholar 

  8. Teguh, S. C.; Klonis, N; Duffy, S.; Lucantoni, L.; Avery, V. M.; Hutton, C. A. Baell, J. B.; Tilley, L. J. Med. Chem. 2013, 56, 6200.

    Article  CAS  Google Scholar 

  9. Hinkov, A.; Yosifova, L.; Todorova, E.; Raleva, S.; Pavlov, A.; Chervenkov, S.; Dundarova, D.; Argirova, R. Auton. Autacoid Pharmacol. 2010, 30, 107.

    CAS  Google Scholar 

  10. (a) Aksenov, A. V.; Smirnov, A. N.; Aksenov, N. A.; Aksenova, I. V.; Matheny, J. P.; Rubin, M. RCS Adv. 2015, 5, 8647. (b) Aksenov, A. V.; Smirnov, A. N.; Aksenov, N. A.; Aksenova, I. V.; Bijieva, A. S.; Rubin, M. Org. Biomol. Chem. 2014, 12, 9786. (c) Aksenov, A. V.; Smirnov, A. N.; Aksenov, N. A.; Aksenova, I. V.; Frolova, L. V.; Kornienko, A.; Magedov, I. V.; Rubin, M. Chem. Commun. 2013, 49, 9305.

  11. Aksenov, A.; Smirnov, A.; Magedov, I.; Reisenauer, M.; Aksenov, N.; Aksenova, I.; Pendleton, A.; Nguyen, G.; Johnston, R.; Rubin, M.; De Carvalho, A.; Kiss, R.; Mathieu, V.; Lefranc, F.; Correa, J.; Cavazos, D.; Brenner, A.; Bryan, B.; Rogelj, S.; Kornienko, A.; Frolova, L. J. Med. Chem. 2015, 58, 2206.

    Article  CAS  Google Scholar 

  12. Bahner, C. T.; Kinder, H.; Gutman, L. J. Med. Chem. 1965, 8, 397.

    Article  CAS  Google Scholar 

  13. De Silva, S. O.; Snieckus, V. Can. J. Chem. 1974, 52, 1294.

    Article  Google Scholar 

  14. Wang, S.; Kim, Y. K.; Chang, Y.-T. J. Comb. Chem. 2008, 10, 460.

    Article  CAS  Google Scholar 

  15. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

Download references

Financial support to this program was provided by the Council for Grants of the President of the Russian Federation for Support of Young Russian Scientists with PhD degree (MK-5733.2015.3).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Alexander V. Aksenov or Michael A. Rubin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 865–869

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aksenov, A.V., Nadein, O.N., Aksenov, N.A. et al. Microwave synthesis of 2-[(E)-2-(1H-indol-3-yl)vinyl]hetarenes. Chem Heterocycl Comp 51, 865–868 (2015). https://doi.org/10.1007/s10593-015-1788-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1788-0

Keywords

Navigation