Activated manganese dioxide as an oxidizing agent for the conversion of N-methylphenanthrolinium salts to N-methylphenanthrolones | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7820924

Reference Type

Journal Article

Title

Activated manganese dioxide as an oxidizing agent for the conversion of N-methylphenanthrolinium salts to N-methylphenanthrolones

Author(s)

Johnson, MR; Bell, D; Shanaman, L

Year

1997

Is Peer Reviewed?

Yes

Journal

Heterocycles
ISSN: 0385-5414

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

1059-1067

DOI

10.3987/COM-96-7727

Web of Science Id

WOS:A1997XJ90000004

URL

http://www.heterocycles.jp/library/abstract.php?doi=06474
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Abstract

Activated manganese dioxide (MnO2) in dry THF was studied for the transformation of N-alkylpyridinium salts to N-alkyl-2-pyridones. Only cations of fused ring pyridines (1,10-phenanthroline, quinoline, etc.) were investigated. Nearly quantitative conversion to 1-methyl-1,10-phenanthrol-2-one was achieved under optimum conditions. Oxidative cleavage of ring methyl groups when present also led to pyridones, in some cases producing a 4-pyridone. Different counteranions gave mixed results. Overall, activated MnO2 is an effective alternative to aqueous ferricyanide for the conversion of fused ring pyridinium salts to the corresponding 2-pyridones.