10027/22503
VR Sabbasani
VR
Sabbasani
H Lee
H
Lee
P Xie
P
Xie
Y Xia
Y
Xia
D Lee
D
Lee
Cyclization of Ynamide-Tethered 1,3,8-Triynes
University of Illinois at Chicago
2018
1,3-diyne cyclization hydride transfer keteniminium pyranopyridine ynamide
2018-06-28 00:00:00
Journal contribution
https://indigo.uic.edu/articles/journal_contribution/Cyclization_of_Ynamide-Tethered_1_3_8-Triynes/10768586
A facile thermal cyclization of ynamide-tethered 1,3,8-triynes to form a 3,5,6,7-tetrahydro-1H-pyrano[3,4-c]pyridine skeleton is described. Although the mechanism of this unusual reaction has yet to be defined, the formation of either a strained keteniminium or a biradical intermediate followed by a 1,5-hydride or -hydrogen shift is tentatively proposed as the key elementary steps in the reaction sequence. Appropriate electronic activation at the carbon center donating a hydride or hydrogen is crucial for successful cyclization. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim