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Published on: February 7, 2019
Base-Mediated Cyclization of N-Benzyl Ketimines with Diynes: Conditions-Controlled Switching between N-Vinyl Pyrroles
Ivan A Bidusenko1, Elena Yu Schmidt1, Igor A Ushakov1
1A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033Irkutsk, Russia.
Abstract:
Semistabilized azaallyl anions, generated from N-benzyl ketimines in the NaOtBu/DMSO superbase medium, undergo conditions-controlled formal [3 + 2] or [4 + 3] cyclization with diaryldiynes. Consequently, selective switchable syntheses of triarylsubstituted α-arylated N-vinyl pyrroles (in up to 64% yield) and tetraarylated 2H-azepines (in up to 75% yield) have been developed. The synthetic value of this strategy has been validated by successful gram-scale syntheses of both products.
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