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Cyclization of Ynamide-Tethered 1,3,8-Triynes

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posted on 2018-06-28, 00:00 authored by VR Sabbasani, H Lee, P Xie, Y Xia, D Lee
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


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This is the pre-peer reviewed version of the following article: Sabbasani, V. R., Lee, H., Xie, P., Xia, Y. and Lee, D. Cyclization of Ynamide-Tethered 1,3,8-Triynes. Chemistry - A European Journal. 2017. 23(34): 8161-8165. 10.1002/chem.201701781. Article, which has been published in final form at


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