N-Alkylation of phenethylamine and tryptamine

Gerta Cami-Kobeci, Paul A Slatford, Michael K Whittlesey, Jonathan M J Williams

Research output: Contribution to journalArticle

  • 82 Citations

Abstract

A clean and efficient method for the N-alkylation of tryptamine and phenethylamine, employing alcs. as the alkylating agents, has been developed. The reaction proceeds via catalytic electronic activation, involving an iridium catalyst which activates the alc. by borrowing hydrogen from the substrate, returning it later in the catalytic cycle. Some examples of N-heterocyclization have been performed employing a diol as the substrate.
LanguageEnglish
Pages535-537
Number of pages3
JournalBioorganic & Medicinal Chemistry Letters
Volume15
Issue number3
StatusPublished - 2005

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Iridium
Alkylating Agents
Alkylation
Hydrogen
Substrates
Chemical activation
Catalysts
phenethylamine
tryptamine

Keywords

  • Glycols Role
  • RACT (Reactant or reagent) (N-heterocyclization via reaction of diols with tryptamine)
  • alkylation phenethylamine tryptamine alc iridium catalyst
  • Alkylation
  • RCT (Reactant)
  • RACT (Reactant or reagent) (N-alkylation of phenethylamine and tryptamine by alcs. catalyzed by iridium complex)
  • PREP (Preparation)
  • heterocyclization diol reaction tryptamine
  • Alcohols Role
  • Heterocyclization (N-heterocyclization via reaction of diols with tryptamine)
  • Amines Role
  • Alkylation catalysts (N-alkylation of phenethylamine and tryptamine by alcs. catalyzed by iridium complex)
  • SPN (Synthetic preparation)

Cite this

N-Alkylation of phenethylamine and tryptamine. / Cami-Kobeci, Gerta; Slatford, Paul A; Whittlesey, Michael K; Williams, Jonathan M J.

In: Bioorganic & Medicinal Chemistry Letters, Vol. 15, No. 3, 2005, p. 535-537.

Research output: Contribution to journalArticle

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PY - 2005

Y1 - 2005

N2 - A clean and efficient method for the N-alkylation of tryptamine and phenethylamine, employing alcs. as the alkylating agents, has been developed. The reaction proceeds via catalytic electronic activation, involving an iridium catalyst which activates the alc. by borrowing hydrogen from the substrate, returning it later in the catalytic cycle. Some examples of N-heterocyclization have been performed employing a diol as the substrate.

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