Journal
TETRAHEDRON
Volume 67, Issue 20, Pages 3603-3611Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.029
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Funding
- National Science Foundation [CHE 0611096]
- American Chemical Society [40665-AC1]
- NSF-EPSCoR [1002165R]
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A selective methodology for the synthesis of either 3-cyanoindoles or 4-cyanoquinolines via a base-modulated palladium-catalyzed reductive N-heterocyclization from a common 1-cyano-1-(2-nitrophenyl)-1-alkene precursor is described. The required starting materials were prepared either by a Kosugi Migita Stille coupling of 2-halo-1-nitrobenzenes with a tributyl(1-alkenyl)stannane or by a vicarious nucleophilic substitution (VNS) of nitrobenzenes followed by a Knoevenagel condensation with an aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.
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