Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 41, Pages 6239-6245Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701321
Keywords
Nitrogen heterocycles; Radical reactions; Alkylation; Hydroxymethylation; Peroxides
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology in Japan [15K05418]
- Grants-in-Aid for Scientific Research [15K05418] Funding Source: KAKEN
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Quinolines and isoquinolines were treated with Na2S2O8 in a mixture of methanol and water at 70 degrees 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.
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