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.
Similar content being viewed by others
References
(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.
Wang, M.; Gao, M.; Miller, K. D.; Sledge, G. W; Hutchins, G. D.; Zheng, Q.-H. Eur. J. Med. Chem. 2009, 44, 2300.
Li, Q. Chang, Y.-T. Nat. Protoc. 2006, 1, 2922.
(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.
Li, Q.; Kim, Y.; Namm, J.; Kulkarni, A.; Rosania, G. R.; Ahn, Y.-H.; Chang, Y.-T. Chem. Biol. 2006, 13, 615.
(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.
Barresi, V.; Bonaccorso, C.; Consiglio, G.; Goracci, L.; Musso, N.; Musumarra, G.; Satriano, C.; Fortuna, C. G. Mol. BioSystems 2013, 9, 2426.
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.
Hinkov, A.; Yosifova, L.; Todorova, E.; Raleva, S.; Pavlov, A.; Chervenkov, S.; Dundarova, D.; Argirova, R. Auton. Autacoid Pharmacol. 2010, 30, 107.
(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.
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.
Bahner, C. T.; Kinder, H.; Gutman, L. J. Med. Chem. 1965, 8, 397.
De Silva, S. O.; Snieckus, V. Can. J. Chem. 1974, 52, 1294.
Wang, S.; Kim, Y. K.; Chang, Y.-T. J. Comb. Chem. 2008, 10, 460.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
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
Corresponding authors
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 865–869
Rights and permissions
About this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-015-1788-0