Infoscience

Journal article

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)]

    Keywords: benzylamine monoamine oxidase inhibitor prepn; propynylbenzodioxolemethanamine prepn monoamine oxidase inhibitor; benzodioxolemethanamine propynyl prepn monoamine oxidase inhibitor

    Note:

    CAN 129:260366

    28-5

    Heterocyclic Compounds (More Than One Hetero Atom)

    Inst. Chimie Organique,Univ. Batiment Chimie,Lausanne-Dorigny,Switz.

    Journal

    0040-4020

    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)

    Reference

    • LSCO-ARTICLE-1998-007

    Record created on 2006-03-03, modified on 2016-08-08

Fulltext

  • There is no available fulltext. Please contact the lab or the authors.

Related material