A Novel Synthesis of Indoel Derivatives

1-Acetyl-2,3-dihydro-5,6-dimethoxy-lg-indole ( 2 ) was synthesized by cyclization of g-(2-bromo-4,5-dimethoxyphenethy1)- acetamide using sodium hydride and cuprous halide in dimethylformamide.Indoles (kt, JJ and &k) were prepared in a similar manner from the corresponding amides (t and & !I )and the carbamate ( & < I .Under similar reaction conditions, phenylacetamides ( @ and afforded the oxindoles ($2 and £2).Recently several reports have appeared in which indoles were synthesized using reactions catalyzed by organometallic compounds such as nickel and palladium 1 complexes .Previously, in the course of synthetic approaches to the mitomycins, we developed a new intramolecular nucleophilic aromatlc substitution reaction using sodium hydride and cuprous bromide in dimethylformamide.The aryl halides(&) and (3) % were thus converted to pyrroloI1,Z-alindoles and (2)2brespective-