We gratefully acknowledge Indiana University Purdue University Indianapolis for financial support. The Bruker 500 MHz NMR was purchased using funds from an NSF-MRI award (CHE-0619254).
Copper-Catalyzed Aerobic Dehydrogenative Cyclization of N-Methyl-N-phenylhydrazones: Synthesis of Cinnolines†
Article first published online: 10 JUL 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 33, pages 8318–8321, August 13, 2012
How to Cite
Zhang, G., Miao, J., Zhao, Y. and Ge, H. (2012), Copper-Catalyzed Aerobic Dehydrogenative Cyclization of N-Methyl-N-phenylhydrazones: Synthesis of Cinnolines . Angew. Chem. Int. Ed., 51: 8318–8321. doi: 10.1002/anie.201204339
- Issue published online: 7 AUG 2012
- Article first published online: 10 JUL 2012
- Manuscript Received: 4 JUN 2012
- NSF. Grant Number: CHE-0619254
- CC coupling;
- synthetic methods
O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a CH bond functionalization process (see scheme; DMF=N,N′-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.