N-aryle oxazolidinones, oxazolidinethiones and...

C - Chemistry – Metallurgy – 07 – D

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C07D 207/02 (2006.01) C07C 41/03 (2006.01) C07C 41/26 (2006.01) C07C 43/178 (2006.01) C07C 309/73 (2006.01) C07D 207/08 (2006.01) C07D 207/26 (2006.01) C07D 207/277 (2006.01) C07D 263/16 (2006.01) C07D 263/20 (2006.01) C07D 263/24 (2006.01) C07D 277/14 (2006.01)

Patent

CA 1129859

ABSTRACT OF THE DISCLOSURE Novel compounds of formula: Image (I) and their preparation. Depending on the meanings of the substituents the preparations include: Condensing a compound of formula: Image with an acid chloride of formula: R3COCl. Submitting a compound of formula: Image to a "phase transfer" reaction, in the presence or a "phase transfer catalyst", in a basic medium with a derivative of formulae: Image Condensing a compound of formula: Image (VIII) with a chloride or tosylate of formula: Image Reacting acrylonitrile in the presence of triton B with the compound of formula (VIII). Condensing a chlorohydrin of formula: Image with phosgene, then condensing the obtained compound with a compound of formula: Image and then cyclising the compound thus obtained by means of ethanolic potash or sodium methylate in methanolic solution. When (I) has the structure: Image (Ia) R(-) submitting to a phase transfer reaction a compound of absolute confi- guration R(-) and of formula: Image (IIb) in the presence of a phase transfer catalyst, of (CH3)2SO4 and in a basic medium. When (I) has the structure: Image (Ib) , S (+) condensing the compound of absolute configuration R and of formula: Image with phosgene, then condensing the obtained compound with p-(cyano-3) benzyloxyaniline, and then cyclising the compound thus obtained by means of ethanolic potash or sodium methylate in methanolic solution. Re- acting an amine of formula Image with a compound of formula: Image Reacting a metanitrobenzyl chloride on a compound of formula: Image Reducing with lithium aluminum hydride the compound of formula: Image Cyclising by means of phosgene the compound of formula: Image Cyclising by means of thiophosgene, either a compound of formula: Image or a compound of formula: Image Condensing an acid chloride of formula: R18COCl with a compound of formula (I) having the structure Image The compounds of formula (I) are antidepressants.

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