Journal
TETRAHEDRON
Volume 63, Issue 14, Pages 3049-3056Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.01.058
Keywords
lactam; pyrrole; reduction; oxidative aromatisation
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A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.
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