Synthesis of tetrahydroselenophene derivatives by electrophilic cyclization of 1-butylseleno-4-alkynes

Synthesis of tetrahydroselenophene derivatives by electrophilic cyclization of 1-butylseleno-4-alkynes

Gai, Rafaela; Schumacher, Ricardo F.; Zeni, Gilson

Abstract:

Selenophene heterocycles and their derivatives have numerous uses in the fields of biochemistry, physical organic chemistry, material chemistry and organic synthesis. For example, selenophenes are widely studied agents with a diverse array of biological effects, these include antioxidant action, antinociceptive and antiinflammatory properties. A great number of these heterocycles have been synthesized and their chemistry has attracted a good deal of interest and activity from a variety of standpoints. However, the synthetic study of an unsaturated version, tetrahydroselenophene derivatives of selenophenes, has been surprisingly limited. In this way, the electrophilic cyclization appears as an alternative route to generate highly functionalized heterocycles, including selenophene derivatives. This methodology takes advantage, in the most of cases, by the presence of an halogen atom suitable to suffer further transformations. The purpose of this study was to report the convenient synthesis of novel tetrahydroselenophene ring systems 2 starting from 1-butylseleno-4-alkynes 1 (Figure 1).

Selenophene heterocycles and their derivatives have numerous uses in the fields of biochemistry, physical organic chemistry, material chemistry and organic synthesis. For example, selenophenes are widely studied agents with a diverse array of biological effects, these include antioxidant action, antinociceptive and antiinflammatory properties. A great number of these heterocycles have been synthesized and their chemistry has attracted a good deal of interest and activity from a variety of standpoints. However, the synthetic study of an unsaturated version, tetrahydroselenophene derivatives of selenophenes, has been surprisingly limited. In this way, the electrophilic cyclization appears as an alternative route to generate highly functionalized heterocycles, including selenophene derivatives. This methodology takes advantage, in the most of cases, by the presence of an halogen atom suitable to suffer further transformations. The purpose of this study was to report the convenient synthesis of novel tetrahydroselenophene ring systems 2 starting from 1-butylseleno-4-alkynes 1 (Figure 1).

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DOI: 10.5151/chempro-14bmos-R0356-1

Referências bibliográficas

• [1] 1 Rhoden, C. R. B.; Zeni, G. Org. Biomol. Chem, 2011, 9, 1301.
• [2] 2 (a) Meotti, F. C.; Silva, D. O. Santos, A. R. S.; Zeni, G.; Rocha, J. B. T. Nogueira, C. W. Environ. Toxicol. Pharmacol. 2003, 37, 37. (b) Gonçales, C. E. P.; Araldi, D.; Panatieri, R. B.; Rocha, J. B. T.; Zeni, G.; C.W. Nogueira Life Sci. 2005, 76, 2221.
• [3] 3 (a) Stein, A. L.; Alves, D.; da Rocha, J. T.; Nogueira, C. W.; Zeni, G. Org. Lett. 2008, 10, 4983. (b) Alves, D.; Prigol, M.; Nogueira, C. W.; Zeni, G. Synlett 2008, 6, 914. (c) Bui, C. T.; Flynn, B. L. J. Comb. Chem. 2006, 8, 163.
• [4] 4 Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937.

Como citar:

Gai, Rafaela; Schumacher, Ricardo F.; Zeni, Gilson; "Synthesis of tetrahydroselenophene derivatives by electrophilic cyclization of 1-butylseleno-4-alkynes", p-356-356. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0356-1