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Synthesis of ?-substituted tryptamines by regioselective ring opening of aziridines.


ABSTRACT: Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce ?-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

SUBMITTER: Kidd J 

PROVIDER: S-EPMC4930112 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines.

Kidd Jesse J   Maiden Kristen K   Morgan Jeremy B JB  

Tetrahedron 20160601 26


Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions. ...[more]

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