| Autor: |
Preux Y; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Jiao W; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Eyer LN; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Waitaiki-Curry H; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Cameron SA; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Painter GF; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand., Anderson RJ; Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, 5010, New Zealand. |
| Abstrakt: |
α-Azido ketones and their vinylogous relatives β-alkoxy-γ-azido enones are versatile building blocks for constructing diverse heterocyclic products, but are prone to azide decomposition. Here, we report their condensation with propargylic amines and investigate the fate of the intermediate azido-enamine condensation products, both experimentally and theoretically. Efficient intramolecular cycloaddition was observed for electron-poor azide substrates, and a range of diversely substituted [1,2,3]triazolo[1,5- a ]pyrazine products is reported. For electron-rich substrates, azide decomposition predominated. Computational modeling of possible pathways from the azido-enamine intermediates revealed two alternative mechanisms for azide decomposition, which were consistent with observed side products. |
