The organometallic route to benzylamine type monoamine oxidase inhibitors
N-Methyl-N-(2-propynyl)piperonylamine can be simultaneously lithiated at the terminal acetylenic and at that arom. position which is flanked by both the side chain and an oxygen atom. Under carefully established conditions, the metal occupying the latter ortho position can be selectively replaced by an electrophile. In general, it is however more convenient and also more efficacious to protect the acetylenic site by silylation. Then lithium may be introduced into the double-ortho position either by hydrogen/metal or by halogen/metal exchange, using 2-bromo-N-methyl-N-[(3-trimethylsilyl)-2-propynyl]piperonylamine as the starting material in the latter case. One of the new products, i.e., 4-bromo-N-methyl-N-(2-propynyl)-1,3-benzodioxole-5-methanamine (piperonal deriv.), proved to be a strong monoamine oxidase (MAO) inhibitor. [on SciFinder (R)]
1998
54
34
10119
10124
CAN 129:260366
28-5
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chimie Organique,Univ. Batiment Chimie,Lausanne-Dorigny,Switz.
Journal
written in English.
9001-66-5 (Monoamine oxidase) Role: BPR (Biological process), BSU (Biological study, unclassified), BIOL (Biological study), PROC (Process) (inhibitors; prepn. of benzylamine type monoamine oxidase inhibitors via organometallic route); 213485-05-3P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. of benzylamine type monoamine oxidase inhibitors via organometallic route); 106-96-7 (Propargyl bromide); 120-57-0 (Piperonal) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of benzylamine type monoamine oxidase inhibitors via organometallic route); 56862-18-1P; 213485-04-2P; 213485-07-5P; 213485-08-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of benzylamine type monoamine oxidase inhibitors via organometallic route); 213485-06-4P; 213485-09-7P; 213485-10-0P; 213485-11-1P; 213485-12-2P; 213485-13-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of benzylamine type monoamine oxidase inhibitors via organometallic route)
REVIEWED
EPFL