SynOpen, Table of Contents CC BY-NC-ND 4.0 · SynOpen 2022; 06(03): 173-178DOI: 10.1055/a-1896-3987 letter MnVI-NP–Catalyzed Generation of Nitrile Oxides: Easy Access to Isoxazolines and Isoxazoles via Stereoselective 1,3-Dipolar Cycloaddition Reactions Authors Author Affiliations Yasmin Saima a Vivekananda College, Madhyamgram, India Saikat Khamarui ∗ b Government General Degree College, Kalna-1, India Recommend Article Abstract All articles of this category(opens in new window) Abstract The versatility and effectiveness of MnVI-NPs as a catalyst is examined for the generation of nitrile oxides from aldoximes and subsequent 1,3-dipolar cycloaddition reactions. This synthetic protocol features fast reaction convergence under benign reaction conditions, operational simplicity, and the use of inexpensive precursors; it avoids the use of acids or bases. The strategy offers excellent chemo-, regio-, and diastereoselectivity in the 1,3-dipolar cycloaddition reaction of in situ generated nitrile oxides with alkenes and alkynes. Key words Key wordsmanganese - nanoparticles - nitrile oxides - 1,3-dipolar cycloadditions - isoxazolines - isoxazoles Full Text References References and Notes 1a Sun S, Murray CB, Weller D, Folks L, Moser A. Science 2000; 287: 1989 1b Yi G, Lu H, Zhao S, Ge Y, Yang W, Chen D, Guo L.-H. Nano Lett. 2004; 4: 2191 1c Hu A, Yee GT, Lin W. J. Am. Chem. Soc. 2005; 127: 12486 1d Turner M, Golovko VB, Vaughan OP, Abdulkin HP, Berenguer-Murcia A, Tikhov MS, Johnson BF. G, Lambert RM. Nature 2008; 454: 981 1e Sokolova V, Epple M. Angew. Chem. Int. Ed. 2008; 47: 1382 1f Sperling RA, Gil PR, Zhang F, Zanella M, Parak W. J. Chem. Soc. Rev. 2008; 37: 1896 1g Riha SC, Johnson DC, Prieto AL. J. Am. Chem. Soc. 2011; 133: 1383 1h Gayen KS, Sengupta T, Saima Y, Das A, Maiti DK, Mitra A. Green Chem. 2012; 14: 1589 2a Lee YS. 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The combined organic extracts were washed with water (3 × 30 mL) and brine (1 × 30 mL) and then dried over anhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure at room temperature. The residue was purified by column chromatography over silica gel (60–120 mesh) with ethyl acetate–petroleum ether as the eluent to furnish pure Δ2-isoxazoline 3b.3-(3,4-Dichlorophenyl)-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester (3b): Rf = 0.6 (1:4 ethyl acetate–petroleum ether); yield: 76% (218 mg, 0.76 mmol); yellow solid; mp 70 °C. 1H NMR (300 MHz, CDCl3): δ = 1.26 (3 H, t, J = 7.2 Hz), 3.49–3.55 (2 H, m), 4.21 (2 H, q, J = 7.2 Hz), 5.09–5.16 (1 H, m), 7.39–7.68 (2 H, m), 7.78 (1 H, s). 13C NMR (75 MHz, CDCl3): δ = 14.1, 38.4, 62.2, 78.6, 125.9, 126.1, 128.7, 130.9, 133.2, 134.7, 154.3, 169.7. FT-IR (KBr): 1030, 1397, 1734, 3140 cm–1. HRMS: m/z calcd for C12H12Cl2NO3 [M+ + H]: 288.0194; found: 288.0190. 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