Factorial design study to access the "green" iodocyclization reaction of 2-allylphenols

Autor(es)

Correa, Michelle Fidelis ; Ramos Barbosa, Alefe Jhonatas ; Sato, Rie ; Junqueira, Luis Otavio ; Politi, Mario Jose ; Rando, Daniela Goncales ; dos Santos Fernandes, Joao Paulo

• Tipo de documento: Artigo Científico
• Fonte: GREEN PROCESSING AND SYNTHESIS; v. 5, n. 2, p. 7-pg., 2016-04-01.

Resumo

Iodocyclization of 2-allylphenols is a suitable method to access furans and dihydrofurans with adequate yields. Several methodologies to iodocyclization are reported in the literature; however, since some data about the conditions are conflicting, a more systematic approach is needed to define the best conditions. In this work, we performed a full 22 factorial design to study the influence of solvent (water or EtOH: water (1: 9) mixture) and the addition of NaHCO3 in iodine-promoted cyclization of 2-allylphenols. The results have shown water as the best solvent to be employed in the cyclization of liquid 2-allylphenols, and the presence of NaHCO 3 leads to lower yields. Several examples of 2-iodomethyl-2,3-dihydrobenzofurans preparations are reported using the optimized conditions; however, high yields are only observed when liquid 2-allylphenols were used. (AU)

• Processo FAPESP: 13/20479-9 - Síntese e avaliação de compostos potencialmente ligantes de receptores H4
• Beneficiário: João Paulo dos Santos Fernandes
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/01875-0 - Síntese paralela, screening in vitro e estudos de relação estrutura-atividade de nitroderivados ativos contra patógenos infectantes de macrófagos: Mycobacterium tuberculosis formas NRP e Leishmania sp
• Beneficiário: Daniela Goncales Galasse Rando
• Modalidade de apoio: Auxílio à Pesquisa - Regular