Pd(II)-Catalyzed Annulation Reactions of Epoxides with Benzamides to Synthesize Isoquinolones

  • Org Lett. 2021 Feb 5;23(3):863-868. doi: 10.1021/acs.orglett.0c04097.
Huihong Wang  1 ,  Fei Cao  1 ,  Weiwei Gao  1 ,  Xiaodong Wang  2 ,  Yuhang Yang  2 ,  Tao Shi  2 ,  Zhen Wang  1  2
Affiliations
  • 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, No. 222 South Tianshui Road, Lanzhou 730000, China.
  • 2. School of Pharmacy, Lanzhou University, No. 199 West Donggang Road, Lanzhou 730000, China.
PMID: 33464099 DOI: 10.1021/acs.orglett.0c04097
Abstract

Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C-H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.

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