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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Franco, Marcelo Straesser [1] ; Saba, Sumbal [2] ; Rafique, Jamal [3] ; Braga, Antonio Luiz [1, 4]
Total Authors: 4
Affiliation:
[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
Total Affiliations: 4
Document type: Journal article
Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 60, n. 34 JUL 2021.
Web of Science Citations: 0
Abstract

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)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program