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Open access visualization of Workflow, Chemical Structure, Nitrogen-to-carbon exchange, Pyridines, X-ray
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Formal nitrogen-to-carbon exchange of pyridines and X-ray of Tf N -Zincke imine Im9 . Reaction conditions: a Pyridines (0.2 mmol, 2.0 equiv.), Tf 2 O (0.2 mmol, 2.0 equiv.), ethyl acetate (1.0 mL), -78 C, 0.5 h, then dibenzylamine (0.24 mmol, 2.4 equiv.), 2,4,6-collidine (0.2 mmol, 2.0 equiv.), 60 C, 1.0 h. Imine intermediate was isolated by precipitation. Then ketone (0.1 mmol, 1.0 equiv), t BuONa (0.15 mmol, 1.5 equiv), THF (2.0 mL), 100 C, 20 h. b N-C exchange scope. Yields of isolated products are shown. b Imine intermediate was not isolated. *Yields of isolated imines. Modified reaction conditions: c NaHMDS was used instead of t BuONa. c Distinctive 13 C-NMR spectra of [ 13 C 1 ]benzophenone (NMR solvent: CDCl 3 ). d Nicotine modification with N-C exchange procedure. e [ 2 H 5 , 13 C 1 ]benzophenone reduction to afford diarylmethylpiperazine drug intermediate.

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