The first synthesis of isoxazolo[3, 4-c]pyridine-7-ones. Issue 39 (28th September 2016)

• Record Type: Journal Article
• Authors: Csimbók, Ervin; Takács, Daniella; Balog, József A.; Egyed, Orsolya; May-Nagy, Nóra V.; Keserű, György Miklós
• Is Part Of: Tetrahedron letters. Volume 57:Issue 39(2016)
• Page Start: 4401
• Page End: 4404
• Publication Date: 2016-09-28
• Subjects: Isoxazolo[3, 4-c]pyridine-7-one -- New heterocyclic ring system -- Lead oriented synthesis -- Medicinal chemistry; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Isoxazolo[3, 4- c ]pyridine-7-ones are interesting scaffolds for medicinal chemistry. The first synthesis of these novel heterocyclic ring systems is reported. The crystal structures support their use in drug discovery programmes. Abstract: During the lead-oriented synthesis of new heterocycles, ethyl 4-(cyanomethyl)-5-phenylisoxazole-3-carboxylate was identified as a key intermediate towards the synthesis of new isoxazolo[3, 4- c ]pyridine scaffolds. The key reaction was the catalytic hydrogenation of ethyl 4-(cyanomethyl)-5-phenylisoxazole-3-carboxylate using Raney/Ni followed by a selective ring closure reaction to afford 3-phenylisoxazolo[3, 4- c ]pyridin-7(6 H )-one and its unsaturated analogue as new ring systems with lead-like properties.