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