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

MARTINS, G; ZENI, G; DAVID F. BACK; KAUFMAN, T. S.; SILVEIRA, C. C.

ADVANCED SYNTHESIS & CATALYSIS (PRINT)

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2015 vol. 357 p. 3255 - 3261

1615-4150

Afacile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis ofpolysubstituted 3H-benzo[e]indoles is reported. The transformation wasoptimized and the best results were obtained by using iodine (1.2 equiv,) indichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstitutedpyrroles were efficiently obtained by means of a nickel (II) chloride-promotedfour-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethylacetoacetate) reaction. Further functionalization of the resulting5-iodoheterocycles was also explored.