FeCl3-Diorganoyl Dichalcogenides Promoted Cyclization to Fused 4-Substituted selenophenes[2,3-b]thiophenes

FeCl3-Diorganoyl Dichalcogenides Promoted Cyclization to Fused 4-Substituted selenophenes[2,3-b]thiophenes

Stein, André L.; Rosário, Alisson R.; Bilheri, Filipe N.; Nogueira, Cristina W.; Zeni, Gilson

Abstract:

The derivatives of fused heterocycles are valued not only for their rich and varied chemistry, but also for many important biological properties. The synthesis of fused heterocycles has also attracted considerable attention because of their use in the synthesis of a variety of functional materials for electronic devices. Among chalcogenides, fused chalcogenophene derivatives play an important role in organic synthesis because of their excellent electrical properties and environmental stability. Thus, during the past years there has been an impressive increasing attention in the development of environmentally benign protocols and the great challenge for chemists is to apply cost-effective, green, mild, and alternative methodologies. In this context, iron has appeared as a versatile alternative, due to its low price, nontoxicity, and environmentally benign properties. Considering these aspects and the large number of methodologies which have successfully used FeCl3 in the synthesis of interesting heterocycle or carbocycle compounds, the purpose of this study was to report the convenient one-step synthesis of novel fused heterocyclic ring systems containing selenothiophene moiety 2, starting from 2- organochalcogen-3-alkynylthiophenes 1 (Figure 1).

The derivatives of fused heterocycles are valued not only for their rich and varied chemistry, but also for many important biological properties. The synthesis of fused heterocycles has also attracted considerable attention because of their use in the synthesis of a variety of functional materials for electronic devices. Among chalcogenides, fused chalcogenophene derivatives play an important role in organic synthesis because of their excellent electrical properties and environmental stability. Thus, during the past years there has been an impressive increasing attention in the development of environmentally benign protocols and the great challenge for chemists is to apply cost-effective, green, mild, and alternative methodologies. In this context, iron has appeared as a versatile alternative, due to its low price, nontoxicity, and environmentally benign properties. Considering these aspects and the large number of methodologies which have successfully used FeCl3 in the synthesis of interesting heterocycle or carbocycle compounds, the purpose of this study was to report the convenient one-step synthesis of novel fused heterocyclic ring systems containing selenothiophene moiety 2, starting from 2- organochalcogen-3-alkynylthiophenes 1 (Figure 1).

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0355-1

Referências bibliográficas

• [1] 1 F. Manetti, A. Santucci, G. A. Locatelli, G. Maga, A. Spreafico, T. Serchi, M. Orlandini, G. Bernardini, N. P. Caradonna, A. Spallarossa, C. Brullo, S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, O. Hoffmann, M. Bologna, A. Angelucci, M. Botta, J. Med. Chem. 2007, 50, 5579.
• [2] 2 T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds, Handbook of Conducting Polymers, 2nd ed., Dekker, New York, 1998;
• [3] 3 J. Nakayama, T. Konishi, Heterocycles 1988, 27, 1731.
• [4] 4 (a) Cantagrel, G.; Carnavalet, B. C.; Meyer, C.; Cossy, J. Org. Lett. 2009, 11, 4262. (b) Xu, T.; Yu, Z.; Wang, L. Org. Lett. 2009, 11, 2113. (c) Cao, K.; Zhang, F.-M.; Tu, Y.-Q.; Zhuo, X.-T.; Fan, C.-A. Chem.;Eur. J. 2009, 15, 6332.

Como citar:

Stein, André L.; Rosário, Alisson R.; Bilheri, Filipe N.; Nogueira, Cristina W.; Zeni, Gilson; "FeCl3-Diorganoyl Dichalcogenides Promoted Cyclization to Fused 4-Substituted selenophenes[2,3-b]thiophenes", p-355-355. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0355-1