Gold-Catalyzed Synthesis of Diaza-hexatrienes Via Diazo Attack at Vinylgold Carbenes: An Easy Access to 1<i>H</i>-Pyrazolo[4,3-<i>b</i>]pyridine-5-ones
Vikas Ashokrao Sadaphal, Rai‐Shung Liu
Abstract
This work reports a gold-catalyzed stereoselective synthesis of highly substituted E-configured 2,3-diaza-1,3,5-hexatrienes using α-diazo nitriles and cyclopropene derivatives; such products arise from an atypical diazo attack of α-aryldiazo nitriles at vinylgold carbenes. For these 2,3-diaza-1,3,5-hexatrienes, we develop a novel anionic cyclization of derivatives of one family to form 1H-pyrazolo[4,3-b]pyridine-5-ones.
Topics & Concepts
DiazoChemistryStereoselectivityPyridineCatalysisCombinatorial chemistryCyclopropeneMedicinal chemistryCarbeneStereochemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods