Abstract
An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkylation
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Cinnamates / chemistry
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Cyclopropanes / chemical synthesis
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Cyclopropanes / chemistry*
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Imidazoles / chemistry
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Indoles / chemistry
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Methylation
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Molecular Structure
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Monoamine Oxidase / metabolism
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Monoamine Oxidase Inhibitors / chemistry
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Neurotransmitter Agents / chemical synthesis
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Neurotransmitter Agents / chemistry*
Substances
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Cinnamates
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Cyclopropanes
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Imidazoles
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Indoles
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Monoamine Oxidase Inhibitors
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Neurotransmitter Agents
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cinnamic acid
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imidazole
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cyclopropylamine
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Monoamine Oxidase