Journal of Organic Chemistry p. 9480 - 9494 (2015)
Update date:2022-08-11
Topics:
Yoshimatsu, Mitsuhiro
Tanaka, Miki
Fujimura, Yu
Ito, Yukiteru
Goto, Yusuke
Kobayashi, Yuka
Wasada, Hiroaki
Hatae, Noriyuki
Tanabe, Genzoh
Muraoka, Osamu
A protocol for the direct synthesis of azepines using a hafnium(III)-catalyzed [6 + 1] annulation of N-tethered ynenitriles with Reformatsky reagents is reported. A broad range of 3-amino-2,7-dihydro-1H-azepine-4-carboxylates 4aa-4he were obtained in high yields and with excellent functional group tolerance. The copper-mediated reactions of isolable Blaise intermediates (enamino esters 3), uniquely underwent 5-endo cyclization to afford the β-2,5-dihydropyrrolyl α,β-unsaturated esters 5aa-5fc, which exhibit anticancer activity.
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