Publication

The organometallic route to benzylamine type monoamine oxidase inhibitors

Manfred Schlosser
1998
Journal Articles

Abstract

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)]

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https://infoscience.epfl.ch/entities/publication/076f19a9-929a-49e6-b5af-ac2b14c29c25

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Manfred Schlosser
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/076f19a9-929a-49e6-b5af-ac2b14c29c25

About this result

Related concepts (32)

Alkali metal

The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), and francium (Fr). Together with hydrogen they constitute group 1, which lies in the s-block of the periodic table. All alkali metals have their outermost electron in an s-orbital: this shared electron configuration results in their having very similar characteristic properties. Indeed, the alkali metals provide the best example of group trends in properties in the periodic table, with elements exhibiting well-characterised homologous behaviour.

Metal

A metal (from Ancient Greek μέταλλον métallon 'mine, quarry, metal') is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typically ductile (can be drawn into wires) and malleable (they can be hammered into thin sheets). These properties are the result of the metallic bond between the atoms or molecules of the metal. A metal may be a chemical element such as iron; an alloy such as stainless steel; or a molecular compound such as polymeric sulfur nitride.

Metal–halogen exchange

In organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals (Li, Na, Mg) and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds. Two kinds of lithium–halogen exchange can be considered: reactions involving organolithium compounds and reactions involving lithium metal.

Related publications (27)

The organometallic route to benzylamine type monoamine oxidase inhibitors

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