A new strategy for 2-substituted indolylalkylamines: synthesis of 2-aryldihomotryptamines

Substituted homologues of tryptamines were synthesized in one step in high yields under mild conditions. The key intermediates are arylhydrazones of 6-aminohexanones, which undergo Fischer rearrangement readily in glacial acetic acid. An easy and ready for scale-up procedure is developed and formerly unknown 2-substituted dihomotryptamines are obtained.