An expeditious synthesis of isoxazoline using cetyltrimethylammonium cerium nitrate: A phase transferring oxidative 1,3-dipolar cycloaddition

Chinese Chemical Letters

Volumn 21, Issue 11, 2010, Pages 1287-1290

  Kumar, Parvin ^a   Kumar, Ashwani ^b  

^a Guru Nanak Khalsa College   (India)

^b GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

1,3 Dipolar addition; Activated alkene; Cetyltrimethylammonium cerium nitrate; Isoxazoline; Oxime

Indexed keywords

EID: 77957232859     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2010.05.015     Document Type: Article

References (28)

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25. Synthesis of cetyltrimethylammonium cerium (IV) nitrate: Cerium (IV) ammonium nitrate (0.01mol) in 10mL water was added slowly to an aqueous solution of cetyltrimethylammonium bromide (0.025mol) with continuous stirring on a magnetic stirrer. A yellow coloured compound appeared slowly. Stirring was continued for 30min. The resulting yellow coloured compound was filtered with water for several times till no trace of bromide ion was detected in the filtrate. It was vacuum dried and kept in a dark bottle inside desiccator, yield 93%. Anal. Calcd. for C38H84N8O15Ce: C, 42.22; H, 7.77; N, 13.37. Found: C, 42.50; H, 7.96; N, 13.32%.
26. General experimental procedure for synthesis of 3: An aldoxime 1 (1.0mmol) and methyl acrylate/acrylonitrile/vinyl acetate (1.2mmol) were taken in anhydrous CH2Cl2 (25mL). Cetyltrimethylammonium cerium nitrate (2.36g, 2.2mmol) was added and the reaction mixture was stirred at room temperature for the time as indicated in Table 1. The reaction was monitored by TLC. After completion, water (20mL) was added and shaken well. Separated the organic layer and again washed with water (10mL), dried over MgSO4 and concentrated. The residue was subjected to column chromatography over silica gel using hexane-ethylacetate (5:2) as eluent to obtain pure isoxazoline 3. Spectral data of synthesized oxazoline are given below: 3a 1H NMR (CDCl3, 400MHz): δ 8.46 (d, 1H, J=2.1Hz), 8.35 (dd, 1H, J=8.0, 2.1Hz), 8.09 (dd, 1H, J=8.0, 2.0Hz), 7.69 (m, 1H), 5.48 (dd, 1H, J=8.0, 5.8Hz), 3.83 (dd, 1H, J=11.5, 8.0Hz), 3.71 (dd, 1H, J=11.5, 5.8Hz); MS (EI): m/z 217.05 (M+) (Found: C, 55.39; H, 3.33; N, 19.27. C10H7N3O3 requires: C, 55.30; H, 3.25; N, 19.35%). 3b 1H NMR (CDCl3, 400MHz): δ 7.74 (dd, 1H, J=7.9, 2.2Hz), 7.50-7.28 (m, 3H), 5.38 (dd, 1H, J=8.0, 4.3Hz), 3.94 (dd, 1H, J=11.6, 8.0Hz), 3.79 (dd, 1H, J=11.6, 4.3Hz); MS (EI): m/z 206.02, 208.02 (M+) (Found: C, 58.23; H, 3.37; N, 13.44. C10H7ClN2O. requires: C, 58.13; H, 3.41; N, 13.56; %). 3c 1H NMR (CDCl3, 400MHz): δ 7.76 (m, 2H), 7.45 (m, 3H), 5.35 (dd, 1H, J=8.0, 5.7Hz), 3.83 (dd, 1H, J=11.5, 8.0Hz), 3.71 (dd, 1H, J=11.5, 5.7Hz); MS (EI): m/z 172.06 (M+) (Found: C, 69.64; H, 4.78; N, 16.32. C10H8N2O requires: C, 69.76; H, 4.68; N, 16.27%). 3d 1H NMR (CDCl3, 400MHz): δ 8.44 (d, 1H, J=2.2Hz), 8.30 (dd, 1H, J=8.0, 2.2Hz), 8.10 (dd, 1H, J=8.0, 2.0Hz), 7.68 (m, 1H), 5.28 (dd, 1H, J=8.2, 3.8Hz), 3.83 (s, 3H), 3.78 (dd, 1H, J=11.5, 8.2Hz), 3.62 (dd, 1H, J=11.5, 3.8Hz); MS (EI): m/z 250.06 (M+) (Found: C, 52.92; H, 4.12; N, 11.24. C11H10N2O5 requires: C, 52.80; H, 4.03; N, 11.20%). 3e 1H NMR (CDCl3, 400MHz): δ 7.73 (dd, 1H, J=7.9, 2.2Hz), 7.42-7.25 (m, 3H), 5.16 (dd, 1H, J=7.9, 3.9Hz), 3.79 (dd, 1H, J=11.6, 7.9Hz), 3.62 (dd, 1H, J=11.6, 3.9Hz), 3.85 (s, 3H); MS (EI): m/z 239.03, 241.03 (M+) (Found: C, 55.22; H, 4.27; N, 5.74. C11H10ClNO3 requires: C, 55.13; H, 4.21; N, 5.84%). 3f 1H NMR (CDCl3, 400MHz): δ 7.76 (d, 2H, J=7.5Hz), 7.45 (m, 3H), 5.17 (dd, 1H, J=8.1, 4.2Hz), 3.79 (dd, 1H, J=11.6, 8.1Hz), 3.62 (dd, 1H, J=11.6, 4.2Hz), 3.85 (s, 3H); MS (EI): m/z 205.07 (M+) (Found: C, 64.45; H, 5.51; N, 7.02. C11H11NO3 requires: C, 64.38; H, 5.40; N, 6.83%). 3g 1H NMR (CDCl3, 400MHz): δ 8.45 (d, 1H, J=2.2Hz), 8.30 (dd, 1H, J=8.0, 2.2Hz), 8.09 (dd, 1H, J=8.0, 2.0Hz), 7.67 (m, 1H), 6.83 (dd, 1H, J=8.2, 3.8Hz), 3.68 (dd, 1H, J=11.5, 8.2Hz), 3.40 (dd, 1H, J=11.5, 3.8Hz), 2.12, (s, 3H); MS (EI): m/z 250.06 (M+) (Found: C, 52.94; H, 3.97; N, 11.14. C11H10N2O5 requires: C, 52.80; H, 4.03; N, 11.20%). 3h 1H NMR (CDCl3, 400MHz): δ 7.79 (dd, 1H, J=8.1, 1.9Hz), 7.48-7.23 (m, 3H), 6.80 (dd, 1H, J=8.8, 3.9Hz), 3.82 (dd, 1H, J=11.6, 8.8Hz), 3.42 (dd, 1H, J=11.6, 3.9Hz), 2.16 (s, 3H); MS (EI): m/z 239.03, 241.03 (M+) (Found: C, 55.24; H, 4.19; N, 5.92. C11H10ClNO3 requires: C, 55.13; H, 4.21; N, 5.84%). 3i 1H NMR (CDCl3, 400MHz): δ 7.76 (m, 2H), 7.45 (m, 3H), 6.73 (dd, 1H, J=8.6, 3.6Hz), 3.78 (dd, 1H, J=11.6, 8.6Hz), 3.50 (dd, 1H, J=11.6, 3.6Hz), 2.16 (s, 3H); MS (EI): m/z 205.07 (M+) (Found: C, 64.22; H, 5.33; N, 6.98. C11H11NO3 requires: C, 64.38; H, 5.40; N, 6.83%).
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