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Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines - Synthesis of L-695

Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines - Synthesis of L-695

  1. trptamene
    Among biologically active indoles, tryptamines show
    tremendous central nervous system activity. For example,
    the neurotransmitter serotonin (2) [5-hydroxytryptamine
    (5-HT)l is involved in the regulation of various physiological
    functions, such as appetite, sleep, body temperature,
    blood pressure, and sexual behavior;l its N,Ndimethyl
    analogue bufotenine (3) is a hallucinogen. The
    N,N-dimethyltryptamines also act as ~ - H Ta~goDni sts and
    possess great potential for the treatment of migraine.
    Sumatriptan (4) is the first of this class of drugs to be
    approved for this use.2 L-695,894 (11, which contains the
    3-amino-1,2,4-oxadiazoleh eterocycle instead of a sulfonamide,
    is also a potent ~-HTIaDg onist that is a potential
    agent for migraine the rap^.^ We now wish to disclose a
    highly efficient method for the preparation of N,Ndimethyltryptamines
    with application to the synthesis of
    L-695,894

    J. Org. Chem. 1994,59, 3738-3741