A New Short Synthesis of 3-Substituted 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indoles (Amino-CBIs)

  • 10.1021/jo0263115
  • The Journal of Organic Chemistry
  • p 8958-8961, Volume 67, Issue 25,
  • journal-article
A new short synthesis of 3-substituted 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indoles from Martius Yellow is disclosed. The key steps of the synthesis were three efficient regioselective reactions (iodination, 5-exo-trig aryl radical−alkene cyclization and carboxylation).

Review

Efficient and reproducible method to obtain Amino-CBIs

The presented route provides an efficient and highly reproducible method to obtain penultimate allyl-protected intermediates of 3-Substituted 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indoles (amino-CBIs).  De-allylation utilizing Grubbs carbene proved challenging as the...