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Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator

✍ Scribed by P. Desos; B. Serkiz; P. Morain; J. Lepagnol; A. Cordi

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 314 KB
Volume: 6
Category: Article
ISSN: 0960-894X
DOI: 10.1016/s0960-894x(96)00547-1

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✦ Synopsis

Enantioselective reduction of pyrrolo-benzothiadiazine 6 using various chiral reducing agents has been studied and led to efficient synthesis of 8 (S 18986) which was established to be of (S) configuration by single crystal X-ray diffraction analysis. S 18986 is a potent and selective AMPA positive modulator which displays total stereoselectivity, the (R) enantiomer being completely inactive.

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The asymmetric hydrogenation of a dihydropyrrolo-benzothiadiazine dioxide 1 with a diphosphine ruthenium diamine catalyst has been used to synthesize the AMPA receptor positive modulator tetrahydropyrrolo-benzothiadiazine dioxide 2 (S 18986) in high enantiomeric excess. The use of factorial experime