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Hydroxymethylation of Quinolines with Na 2 S 2 O 8 by a Radical Pathway
Author(s) -
Zhou Luan,
Okugawa Naoki,
Togo Hideo
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701321
Subject(s) - chemistry , amide , aldehyde , methanol , hydroxymethyl , radical , tetrazole , transition metal , medicinal chemistry , organic chemistry , catalysis
Quinolines and isoquinolines were treated with Na 2 S 2 O 8 in a mixture of methanol and water at 70 °C to form hydroxymethylated quinolines and isoquinolines in good to moderate yields, under transition‐metal‐free conditions. The formed hydroxymethyl group was smoothly converted into aldehyde, ester, amide, bromomethyl, ( N , N ‐diethylamino)methyl, cyano, and tetrazole groups, in good yields.