Reduction of chromano–piperidine-fused isoxazolidines: Tandem intramolecular rearrangements leading to 2-(methylamino)-4-oxo-N-phenyl-N-propyl-4H-chromene-3-carboxamide. Issue 25 (21st June 2017)

• Record Type: Journal Article
• Authors: Singh, Gagandeep; Gupta, Naman; Gupta, Vivek; Ishar, Mohan Paul Singh
• Is Part Of: Tetrahedron letters. Volume 58:Issue 25(2017)
• Page Start: 2456
• Page End: 2459
• Publication Date: 2017-06-21
• Subjects: 1, 3-Dipolar cycloaddition -- Chromano–piperidine-fused isoxazolidine -- Reductive NO bond cleavage -- Pd/C, HCOONH4 -- Tandem reorganization -- Chromone-3-(N-phenyl)carboxamide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.05.032
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Reductive cleavage of NO bond of isoxazolidines (3a –c ) has been attempted. Reductive NO bond cleavage followed by intra-molecular tandem rearrangements. Providing chromene-3-carboxamide (4 ) having potential medicinal significance. Plausible mechanistic rationale for the formation of compound4 is proffered. Abstract: Reductive ring opening of isoxazolidine moiety of chromano–piperidine-fused isoxazolidines (3a –c ) with HCOONH4 and 10% Pd/C in a mixture of solvents (THF/MeOH) at ambient temperature, affords novel 2-(methylamino)-4-oxo- N -phenyl- N -propyl-4 H -chromene-3-carboxamide (4 ), which is apparently derived from reductive NO bond cleavage followed by tandem intramolecular rearrangements. Plausible mechanistic rationale for the formation of compound4 is proffered.