Pyrroloindoles. 15. Synthesis of tryptamine analogs. 6,7-dihydro-3-(2-phthalimidoethyl)-1h,5h-pyrrolo[2,3-f]indole and 3-(2-phthalimidoethyl)-1H,5H-pyrrolo[2,3-f]indole
Diazotization of 1-acetyl-S-aminoindoline and reaction of the diazonium salt with ethyl α-acetyl-δ-phthalimidovalerate gave the 1-acetyl-5-iruiolhgl hydrazone of ethyl α-keto-δ-phthalimidovalerate. Cyclization of the hydrazone and subsequent hydrolysis, decarboxylation, and dehydrogenation of the pyrroloiruloline gave the corresponding tryptamines.