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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (01): 61-65. Previous Articles     Next Articles

Original Articles

合成文拉法星的2-氮杂-1,3-丁二烯杂Diels-Alder反应与其 单分子环合竞争反应的研究

穆小静a,b; 夏之宁*,a,b; 王春燕a ; Panunzio, Mauroc; 曾礼娜a   

  1. (a重庆大学化学化工学院 重庆 400030)
    (b重庆大学生物工程学院 重庆 400030)
    (c ISOF-CNR Dipartimento di Chimica “G. Camician”Via Selmi, I-40126 Bologna, Italy)
  • 收稿日期:2008-05-12 修回日期:2008-08-13 发布日期:2009-01-20
  • 通讯作者: 夏之宁

Hetero Diels-Alder Reaction versus Intramolecular Cyclization of 2-Aza-butadiene in the Synthesis of Venlafaxine

Mu, Xiaojinga,b; Xia, Zhining*,a,b; Wang, Chunyana ;Panunzio, Mauroc ; Zeng, Lina a
  

  1. (a College of Chemistry & Chemical Engineering, Chongqing University, Chongqing 400030)
    (b College of Biological Engineering, Chongqing University, Chongqing 400030)
    (c ISOF-CNR Dipartimento di Chimica “G. Camician”Via Selmi, I-40126 Bologna, Italy)
  • Received:2008-05-12 Revised:2008-08-13 Published:2009-01-20
  • Contact: Xia, Zhining

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During the hetero Diels-Alder reaction (HAD) between 4-(4-methoxyphenyl)-1-phenyl-3-
(trimethylsilyloxy)-2-aza-butadiene (2-ABDE) and hexanone, a unimolecular [2＋2] cyclization of 2-ABDE forming a four-membered monocyclic β-lactam took place. The reaction parameters such as Lewis acid catalysts, temperature and microwave irradiation on the HDA and [2＋2] reactions have been thoroughly studied. The results show that the competition between the [2＋2] and [4＋2] reactions is largely dependent of temperature. At low temperature as －78 ℃, the product of [4＋2] reaction predominated, while at high temperature as 135 ℃, the product of [2＋2] reaction predominated. Microwave irradiation improved the yield of the [2＋2] reaction significantly. It was also found that the strength and the hardness of the Lewis
acid affected the catalytic ability for the [2＋2] reaction of 2-azabutadiene.

Key words: hetero Diels-Alder reaction, 2-azabutadiene, [2＋2] cyclization, Lewis acid, microwave synthesis