Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas

• Ano de defesa: 2005
• Autor(a) principal: Drekener, Roberta Lopes
• Orientador(a): Bonacorso, Helio Gauze
• Banca de defesa: Braga, Antonio Luiz , Zanatta, Nilo
• Tipo de documento: Dissertação
• 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: Química; Química orgânica; Compostos orgânicos; Compostos heterocíclicos
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/10634

This work describes the reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with substituted anilines 5a-j to obtain a series of N-aril-2-trifluoroacetyl-3,4-diidronaphtalenes (6a-j). Intramolecular cyclization of 6a-j furnished a novel series of substituted 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j). Coumpond 4 was obtained from the trifluoroacetylation reaction of the mixture of acetal (2) and enoléter (3) derived from ketone α-tetralone (1) with trifluoroacetic anhydride. The reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with anilines 5a-j, in molar ratio 1:1, were carried out in acetonitrile at 81oC for 6 hours leading to the compounds 6a-j in 68-87%. The synthesis of 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j) were carried out by intramolecular cyclization reaction of 6a-j in the presence of polyphosphoric acid (PPA), in abscence of organic solvent at 110oC for 24 hours, in 44-82%. Others Lewis acid such as TiCl4, ZnCl2, P2O5/POCl3, POCl3 or CF3COOH and triethylamine were employed to obtain 7a, however only the reactions using PPA gave positive results.