醋酸铜催化“一锅法”合成5-(1-苯基-3-苯基丙基-2-炔基)-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物
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摘要
在醋酸铜催化作用下,以抗坏血酸钠为还原剂,以醛、2,2-二甲基-1,3-二噁烷-4,6-二酮和苯乙炔为原料,通过包含Knoevenagel缩合与Conjugate加成反应的多组分反应,有效地合成了10种5-(1-苯基-3-苯基丙基-2-炔基)-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物.该工艺具有收率高(63%～86%)、反应温和、操作简单及环境友好等优点,为合成5-(3-苯基-1-苯基丙基-2-炔基)-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物提供了一种有效的方法.
In the presence of copper acetate,ten 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized via the three component one-pot reaction of aldehydes with 2,2-dimethyl-1,3-dioxane-4,6-dione and phenylacetylene by using Na-ascorbate as a reductant.The reaction has the advantages of high yields(65%～86%),mild conditions,simple operation and environmental friendliness.It provides an effective method for the synthesis of 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives.
In the presence of copper acetate,ten 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized via the three component one-pot reaction of aldehydes with 2,2-dimethyl-1,3-dioxane-4,6-dione and phenylacetylene by using Na-ascorbate as a reductant.The reaction has the advantages of high yields(65%～86%),mild conditions,simple operation and environmental friendliness.It provides an effective method for the synthesis of 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives.
引文
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[3]Thomas, F.; Knopfel, D. B.; Erick, M. C. Org. Lett. 2004, 6, 2281.
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[5]Shino, U.; Jun-ichi, I.; Ryota, O.; Hisao, N. J. Org. Chem. 2016, 81,3347.
[6]Eriksson,M.;Iliefski,T.;Nilssom,M.;Olsson,T.J.Org.Chem.1997, 62, 182.
[7]Hooz, J.; Layton, R. B. J. Am. Chem. Soc. 1971, 93, 7320.
[8]Pappo, R.; Collin, P. W. Tetrehedron Lett. 1972, 13, 2627.
[9]Sinclair,J.A.;Molander,G.A.;Brown,H.C.J.Am.Chem.Soc.1977, 99, 954.
[10]Kim, S.; Lee, J. M. Tetrehedron Lett. 1990, 31, 7627.
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