Síntese de 4-organocalcogenil-1h-isocromen-1-iminas e 3-(alquil calcogenoil-2-benzofenil[b]selenofeno[2,3-d] calcogenofenos via reações de ciclização mediadas por sais de ferro

• Ano de defesa: 2016
• Autor(a) principal: Santos Neto, José Sebastião dos
• Orientador(a): Zeni, Gilson Rogério
• Banca de defesa: Braga, Antonio Luiz , Morel, Ademir Farias , Botteselle, Giancarlo Di Vaccari , Rodrigues, Oscar Endrigo Dorneles
• Tipo de documento: Tese
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química
• Departamento: Química
• País: BR
• Palavras-chave em Português: Isocromeninimas; Benzocalcogenofenos; Ciclização; Organocalcogênio
• Palavras-chave em Inglês: Isochromeninimes; Benzochalcogenofenes; Cyclization; Organochalcogen
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/4286

In this work we developed the efficient and selective heterocyclic product synthesis using as electrophilic agent a ferric chloride combinated with diorganyl dichalcogenides under mild conditions. In the first part of this work, it was possible a variety of 4-organochalcogenyl-1H-isochromen-1-imines synthesis using a combinated system of diorganyl dichalcogenides and anhydrous ferric chloride using o-alkynylbenzamides as a substrate. These product synhesis given high efficiently and selectivity in 35 for 88% yields. These synthetized products were submeted to palladium coupling reactions leading to expected products in 65 for 80% yields. In a second stage, it was possible a 3-(alkyl chalcogen-2- benzophenyl[b]selenophene[2,3-d] chalcogenophenes using a combinated system with dialkyl diorganyl dichalcogenides and hexahidrate ferric chloride. Through this cyclization protocol we could satisfactorily synthetize a series of benzochalcogenophenes chalcohenofene-fused (35 to 89% yields), using relatively mild reaction condictions, since all the experiments were carried at 39°C under ambient atmosphere.