Palladium-Catalyzed Preparation of N-Substituted Benz[ c, d]indol-2-imines and N-Substituted Amino-1-naphthylamides

J Org Chem. 2022 Jul 1;87(13):8515-8524. doi: 10.1021/acs.joc.2c00620. Epub 2022 Jun 22.

Abstract

Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C-C and C-N coupling of 8-halo-1-naphthylamines with isocyanides in a single step. The reaction features broad substrate scopes and mild conditions, providing an efficient alternative for the construction of antiproliferative agents and BET bromodomain inhibitors. If 0.1 mL of H2O was added to this reaction, the N-substituted amino-1-naphthylamides could be obtained easily.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyanides / chemistry
  • Imines* / chemistry
  • Molecular Structure
  • Palladium* / chemistry

Substances

  • Cyanides
  • Imines
  • Palladium