Journal
TETRAHEDRON
Volume 66, Issue 46, Pages 8968-8973Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.09.037
Keywords
Amidation; One-pot reaction; 1,2-Diketones; Alkali metal reduction
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [21108521 A01]
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Carboxylic acids were heated at 150 degrees C in DMF in the presence of 1.25 equiv of thionyl chloride to give corresponding N,N-dimethylamides in good yields. Tandem chlorination and amidation reactions occurred in the one-pot procedure. Dicarboxylic acids needed prolonged reaction time to produce bis-amides in good yields. Some benzamides were efficiently converted into corresponding 1,2-diaryl-1,2-diketones (benzils) under acyloin condensation conditions in the presence of 4,4'-di-tert-butylbiphenyl (DBB) in THF. Ultrasonic irradiation effectively accelerates the reaction, but it is not critical. However, the presence of DBB is fatal to the reaction. Although a few synthetic methods for benzils from benzoic acids have been reported so far, this method is one of the most convenient and highly reproducible procedures. (C) 2010 Elsevier Ltd. All rights reserved.
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