Radical Bicyclization of N-Phenyl-4-pentenamides: A Modular and Selective Synthesis of γ-Lactam-Substituted
Zeguo Fang1, Hanyang Zhang1, Jiale Hu1
1New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, Wuhan 430068, China.
Abstract:
Herein, we report a modular and efficient silver-catalyzed domino radical bicyclization of N-phenyl-4-pentenamides with 2-(allyloxy)benzaldehydes and 2-allylbenzaldehydes, enabling the selective synthesis of γ-lactam-containing chroman-4-one and indanone hybrids in moderate to good yields. This transformation proceeds under mild conditions and features high step- and atom-economy, constructing two C-C bonds and one C-N bond in a single step within 30 min. Notably, it affords five-membered carbocycles or six-membered oxygen heterocycles with excellent regioselectivity.
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