ol503752k_si_001.pdf (5.73 MB)
Aza-Annulation of Enynyl Azides: A New Approach to Substituted Pyridines
journal contribution
posted on 2015-02-20, 00:00 authored by Chada Raji Reddy, Sujatarani
A. Panda, Motatipally Damoder ReddySynthesis
of substituted pyridines through a novel aza-annulation
of 2-en-4-ynyl azides, derived from MBH-acetates of acetylenic aldehydes,
is described. A variety of enynyl azides having aryl, heteroaryl,
and alkyl groups on the alkyne functionality successfully participated
in the Ag-mediated annulation reaction to provide the corresponding
3,6-disubstituted pyridines. I2-Mediated cyclization was
found to be controlled by the substituent on the alkyne functionality,
which offered the 5-iodo-3,6-disubstituted pyridines from enynyl azides
having an electron-rich substituent on the alkyne functionality.