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

• 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
• 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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