The Kulinkovich reaction in the synthesis of constrained n,n-dialkyl neurotransmitter analogues.
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.
Faler
Catherine A
CA
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.
Joullié
Madeleine M
MM
D000478:Alkylation; D002934:Cinnamates / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D008995:Monoamine Oxidase / Q000378:metabolism; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry; D018377:Neurotransmitter Agents / Q000138:chemical synthesis / Q000737:chemistry*
D002934:Cinnamates; D003521:Cyclopropanes; D007093:Imidazoles; D007211:Indoles; D008996:Monoamine Oxidase Inhibitors; D018377:Neurotransmitter Agents; C029010:cinnamic acid; C029899:imidazole; C067351:cyclopropylamine; D008995:Monoamine Oxidase