Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular

• Autor(a) principal: Grimaldi, Tamíris Bauer
• Data de Publicação: 2016
• Tipo de documento: Tese
• Idioma: por
• Título da fonte: Manancial - Repositório Digital da UFSM
• dARK ID: ark:/26339/00130000106cz
• Texto Completo: http://repositorio.ufsm.br/handle/1/21563
• topic: Carbociclização; Dihidronafto[c]furanos; Fenantrenos; Carboyclization; Dihydronaphtho[c]furans; Phenanthrenes; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA

n this work, we reported the study developed for the preparation of substituted dihydronaphtho[c]furans and phenanthrenes via intramolecular cyclization process. Firstly, a variety of dihydronaphtho[c]furans 2 was prepared by the reaction of bis-propargyl ethers 1 with a catalytic amount of t-BuOK. Subsequently, the o-ethynyl-biphenyls 3 were subjected to carbocyclization reaction mediated by I2 and a catalytic amount of K2CO3, which allowed the synthesis of 9-iodo-10-organochalcogen-phenanthrenes 4. Yet, the o-ethynyl-biphenyls 3 carbocyclization reaction promoted by diorganyl diselenides and FeCl3, lead to 9- organochalcogen-phenanthrenes 5. The methodologies proceeded selectively, furnishing the products in good yields under mild reactions conditions.