Journal of the Chemical Society. Perkin transactions I p. 1929 - 1932 (1984)
Update date:2022-08-02
Topics:
Afsah, El-Sayed M.
Jackson, Anthony H.
A series of new N-indol-3-ylmethylalkylamines (1) have been synthesized in excellent yields via transamination between gramine and the appropriate primary alkylamine.The use of tryptamine and propane-1,3-diamine in the exchange reaction afforded N-indol-3-ylmethyltryptamine (2), and N,N'-bis(indol-3-ylmethyl)propane-1,3-diamine (3) respectively, where as the use of methylamine gave N,N-bis(indol-3-ylmethyl)methylamine (4).The exchange reaction has been extended by the use of amino acids to give N,N-bis(indol-3-ylmethyl)tryptophan (6) and N,N-bis-(indol-3-ylmethyl)glycine (8).The secondary amines (1), (2) and the previously known bis(indol-3-ylmethyl)amine proved to be valuable intermediates for the synthesis of some new compounds related to gramine as well as to other indole alkaloids.
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