Synthesis of Novel KDR Kinase Inhibitors through Catalytic Reductive Cyclization of o-Nitrobenzylcarbonyl Compounds
- 1 October 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (22) , 7761-7764
- https://doi.org/10.1021/jo048843m
Abstract
An efficient synthesis of o-nitrobenzylcarbonyl compounds is demonstrated through the Swern-type oxidation of readily accessible phenethanol analogues. Reductive cyclization of o-nitrobenzylcarbonyl 3 using catalytic Raney nickel gives 1H-indol-2-yl-1H-quinoline 2 in 95% yield. Hydrolysis of 2 affords the KDR kinase inhibitor 1 in quantitative yield. The examination of the reductive cyclization reaction and optimization of conditions is described.Keywords
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