KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach

Autor(es)

Franco, Marcelo Straesser ^[1] ; Saba, Sumbal ^[2] ; Rafique, Jamal ^[3] ; Braga, Antonio Luiz ^{[1, 4]}

Afiliação do(s) autor(es)

^[1] Univ Fed Santa Catarina UFSC, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[2] Univ Fed Goias UFG, Inst Quim, BR-74690900 Goiania, Go - Brazil

^[3] Univ Fed Mato Grosso Sul UFMS, Inst Quim, BR-79074460 Campo Grande, MS - Brazil

^[4] Univ Johannesburg, Dept Chem Sci, Fac Sci, ZA-2028 Doornfontein - South Africa

• Tipo de documento: Artigo Científico
• Fonte: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 60, n. 34 JUL 2021.
• Citações Web of Science: 0

Resumo

Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp(2))-H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo{[}1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields. (AU)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia