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

Author(s)

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

• Document type: Journal article
• Source: GREEN PROCESSING AND SYNTHESIS; v. 5, n. 2, p. 7-pg., 2016-04-01.

Abstract

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)

• FAPESP's process: 13/20479-9 - Synthesis and evaluation of compounds potentially ligands of H4 receptors
• Grantee: João Paulo dos Santos Fernandes
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/01875-0 - Parallel synthesis, in vitro screening and SAR studies of a nitroderivatives compounds library active against macrophage's pathogens: Mycobacterium tuberculosis NRP forms and Leishmania sp
• Grantee: Daniela Goncales Galasse Rando
• Support Opportunities: Regular Research Grants