SYNTHESIS of 4-AMINO-3-CYANO-2-MORPHOLINOQUINOLINE

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Authors	MOHAMED Walid Fathalla MAREK Jaromír PAZDERA Pavel
Year of publication	2002
Type	Article in Periodical
Magazine / Source	Heterocyclic Communications
MU Faculty or unit	Faculty of Science
Citation
Field	Organic chemistry
Keywords	regioselectivity; 4-amino-3-cyano-2-morpholinoquinoline; Thorpe-Ziegler cyclization; 3;1-benzothiazepine; thioureas; sulfur elemination
Description	The 4-amino-3-cyano-2-morpholinoquinoline was obtained via intramolecular Thorpe-Ziegler cyclization of 4-cyano-N4-(2-cyanophenyl)morpholine-4-carboximido-thioate 3 to afford the intermediate 3,1-benzothiazepine 4. Compound 4 undergoes ring contraction to give the quinoline 5 by base catalyzed sulfur atom elimination. IR, 1H, 13C NMR and X-ray structural analysis confirmed the structure of the isolated new products 3 and 5.
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