INTRAMOLECULAR DIELS-ALDER REACTION OF 3-FORMIMIDOYLINDOLES: SYNTHESIS OF FUSED PYRIDOINDOLE COMPOUNDS

Article abstract of DOI:10.3987/COM-92-6191

Intramolecular Diels-Alder reaction of 3-formimidoylindoles having olefinic substituents at the 1-position of the indole ring gave stereoselectively fused pyridoindole compounds.Double bond migration from 2,3,3a,4,12,12a,12b,12c-octahydrobenzindolo<3,2,1-ij><1,6>naphthyridin-11(1H)-ones (4) to 2,3,3a,4,5,12,12a,12b-octahydrobenzindolo<3,2,1-ij><1,6>naphthyridin-11(1H)-one (5) was performed using 10percent Pd-C as a catalyst.