<em>Synthesis Of polyaromatic heterocycles pyrrolo [1,2-a] indoles by Gold(I)-Catalyzed tandem Cyclization/C-H Activation/Cyclization.</em>

Abstract

The initial results on a novel procedure for the synthesis of pyrrolo[1,2-a]indoles via gold(I)-catalyzed tandem cyclization/C-H activation/cyclization is described. The procedure allowed the access to a highly functionalized pyrrolo[1,2-a]indoles in a one-pot process starting from anilinodiynes. The mechanism of this reaction by using gold(I) catalysis, interestingly proceeded via 5-endo-dig cyclization at only one of the alkyne of the diyne fragment, leadig to the formation of 2-alkynylindole derivative. We are purposing a Csp 3 -H bond activation and generating gold(I)carbene species with [1,5]-H migration and cyclization following by [1,2]-H shift. The result we achieved 1-benzhydryl-2-(phenylethynyl)-1-H-indole moiety first cyclization was confirmed by using 1 H, 13 C NMR spectroscopy and X-ray. Interestingly we have developed intramolecular cyclization of indole moiety with high yield, short reaction time and room temperature.