Journal
TETRAHEDRON LETTERS
Volume 45, Issue 25, Pages 4977-4980Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.04.041
Keywords
acylation; anthrapyrazole; hydrazide
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The EDC-mediated condensation of 1-chloro-5-hydrazino-9,10-anthracenedione afforded an N-1 acyl anthrapyrazole instead of the expected hydrazide. The regiochemistry of the N-acyl substituent was assigned on the basis of an extensive set of NMR experiments, and identification of this isomer Suggests a reaction sequence based on initial acylation and Subsequent cyclization. In contrast, the parallel reaction of 1-hydrazino-9,10-anthracenedione proceeded to afford the expected hydrazide. (C) 2004 Elsevier Ltd. All rights reserved.
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