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Updated: Feb 4, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
An Interrupted Schmidt Reaction: C-C Bond Formation Arising from Nitrilium Ion Capture
Manwika Charaschanya1, Kelin Li1, Hashim F Motiwala1
1Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-7363 , United States.
Abstract:
The rerouting of the nitrilium ion formed in the Schmidt reaction of ketones and TMSN3 to encompass C-C bond formation with an electron-rich aromatic group is reported. Thus, when the reaction is carried out in HFIP using AlCl3 or AlBr3 as the promoter, imines, iminium ions, or enamide derivatives are obtained through one-pot procedures. The scope and possible mechanisms of these new transformations are considered.
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