Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
Regioselective Oxidation of Pyrrole Derivatives with DDQ and Its Synthetic Application
Ryoji IwamotoYutaka UkajiKatsuhiko Inomata
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2010 Volume 39 Issue 3 Pages 176-177

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Abstract

t-Butyl 4-alkyl-1H-pyrrole-2-carboxylates were oxidized with DDQ in the presence of MeOH at the α-position of the alkyl substituent at the C-4 position regioselectively to afford 4-acylpyrrole derivatives. On the other hand, treatment of the pyrroles with DDQ in the presence of AcOH furnished the corresponding 4-(1-acetoxyalkyl)pyrroles. The resulting 4-(acetoxymethyl)pyrrole reacted with various nucleophiles to afford the functionalized pyrrole derivatives in good yields.

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© 2010 The Chemical Society of Japan
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