The Reductive Addition Reaction of Substituted 2-Chloromethyl-1,3,4-oxadiazole to Aldehydes and Ketones Promoted by Samarium Diiodide
The Reductive Addition Reaction of Substituted 2-Chloromethyl- 1, 3, 4-oxadiazole to Aldehydes and Ketones Promoted by Samarium Diiodide
摘要
1-（β-Hydroxyalkyl）-l,3,4-oxadiazole derivatives were synthesized via reductive addition reactions of 2-chloromethyl-l,3,4-oxadiazole with carbonyl compounds under mild conditions promoted by SmI2.
1-（β-Hydroxyalkyl）-l,3,4-oxadiazole derivatives were synthesized via reductive addition reactions of 2-chloromethyl-l,3,4-oxadiazole with carbonyl compounds under mild conditions promoted by SmI2.
基金
the National Natural Science Foundation of China(Project No.20072033)
the NSF of Zhejiang Province for financial support.
参考文献6
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2[2]For reviews see: (a) P. G. Steel, J. Chem. Soc. Perkin Trans. 1, 2001, 2727. (b) P. Girard, J.L. Namy, H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693. (c) A. Krief, A. M. Laval, Chem.Rev., 1999, 99, 745. (d) G. A. Molander, Acc. Chem. Res., 1998, 31, 603. (e) G. A.Molander, C. R. Harris, Tetrahedron, 1998, 54, 3321. (f) G. A. Molander, C. R. Harris. Chem Rev., 1996, 96, 307. (g) T. Imamota, Lanthanides in Organic Synthesis, Academic Press,London, 1994, Chapter 4. (h) G. A. Molander, Chem Rev., 1992, 92, 29. (i) D. P. Curran, T.L. Fevig, C. P. Jasperse, M. J. Totleben, Synlett, 1992, 943.
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3[3]2-Chloromethyl-1, 3, 4-oxadiazoles were easily prepared by the literature: H. Kristinsson,Synthesis, 1979, 102.
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5[5]General procedure for the preparation of 1-(β-hydroxyalkyl)-l,3,4-oxadiazole derivatives (3):A solution of 2-chloromethyl-1,3,4-oxadiazole (1 mmol) with aldehydes or ketones (1.2 mmol)in dry THF (3 mL) was added to the solution of SmI2 (2.2 mmol) in THF (20 mL) at room temperature under a nitrogen atmosphere. The deep blue color of the solution immediately changed to yellow. After being stirred for 5 minutes (Table 1, the reaction was monitored by TLC), the reaction mixture was quenched with 0.1 mo1/L hydrochloric acid (5 mL) and extracted with ether (3x15 mL). The organic phase was successively washed with brine (15mL), water (15 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give the crude products, which were purified by preparative TLC using ethyl acetate and cyclohexane (1:2) as eluant.
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6[6]All of the products obtained in this study were characterized (1H NMR, MS, IR, EA). For example, product 3a: m.p. 80-82℃; IR (KBr) v (cm-1): 3312, 2939, 2867, 1623, 1571, 1436,1249, 724; 1H NMR (CDCl3, 400MHz)δ (ppm): 8.04-8.07 (2H, m), 7.51-7.57 (3H, m), 3.13(2H, s), 2.95 (1H, brs), 1.44 (6H, s); MS (70 eV) m/z (%): 219 (M++1, 2.93), 203 (7.93), 160(100), 131 (2.21), 118 (20.32), 77 (39.39); Anal. Calcd. for C12H14N2O2: C 66.04, H 6.47, N12.84; Found C 66.17, H 6.51, N 12.73.
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