Expedient Iodocyclization Approach Toward Polysubstituted 3H‐Benzo[e]indoles

• DOI: 10.1002/adsc.201500275
• Publication Date: 2015-09-28T09:59:02Z
• Authors: Guilherme M. Martins; Gilson Zeni; Davi F. Back; Teodoro S. Kaufman; Claudio C. Silveira
• Keywords: Dichloromethane; Potassium carbonate; Base (topology); Ethyl acetoacetate

Abstract A facile and expedient iodocyclization of 4‐(2‐prop‐1‐ynylphenyl)‐1 H ‐pyrroles towards the synthesis polysubstituted 3 ‐benzo[ e ]indoles is reported. The transformation was optimized best results were obtained by using iodine (1.2 equiv,) in dichloromethane, potassium carbonate as base. starting 1,2,3,4‐tetrasubstituted pyrroles efficiently means a nickel(II) chloride‐promoted four‐component (nitromethane, amine, 2‐alkynylbenzaldehyde ethyl acetoacetate) reaction. Further functionalization resulting 5‐iodoheterocycles also explored. magnified image