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One-pot stereoselective synthesis of dimethanodibenzo[e,i][1,4]diazecines by a zinc-acetic acid promoted cascade reaction

✍ Scribed by Christelle Podevin; Micheline Grignon-Dubois; Gladys Nuissier; Jean-Christophe Gauffre; Bernadette Rezzonico


Book ID
104209501
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
837 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis


The title compounds arc intcrcstiug C> s\nunctric:ll dkm~incs. Thcy uerc prcpared in a one-pot process by reacting quinaldines \vith a zinc-ncctic acid misturc in THF solution. During this simple and slcrcoselectivc process, twvo C-C bonds and 4 stercogcnic centrcs nrc crcntcd undcr mild conditions. hlluc~m of thc concentration of reapnts upon yields aod intrztmolccular cyclkition rcgiochcmistry is dcmonslrntcd. Espcrimcnts using dcukrialed acctic acid allowved a good understanding of IIICSC rcsuhs.