Synthesis of a dihydropyrano[3,2-e]indole as a rotationally restricted phenolic analog of the neurotransmitter serotonin

Article abstract of DOI:10.1016/S0040-4039(00)92702-3

1-(2-Dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole has been synthesized via a six step procedure involving a Claisen rearrangement of a 5-allyloxyindole-3-glyoxamide. This novel heterocycle (1) represents a rotationally restricted phenolic analog of the neurotransmitter [3-(2-aminoethyl)-5-hydroxyindole].