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von Pechman重氮烯烃环加成反应2020-04-28

重氮化合物和烯烃区域选择性的进行1,3-偶极环加成反应关环得到吡唑啉或吡唑的反应。
反应机理
重氮化合物作为1,3-偶极子对烯烃进行1,3-偶极环加成。
反应实例

4-Phenyl-3-trimethylsilylpyrazole (10). A solution of 9 prepared from TMSCHN2 and BuLi was treated with cinnamonitrile 8 (129 mg, 1 mmol) in THF (2 mL). After 0.5 h stirring at -78 ℃ and 1.5 h at -45 ℃, the reaction mixture was quenched with aq NH4Cl. Usual workup and chromatography (silica gel, CHCl3:Et2O, 20:1) gave 190 mg of 10 (88%), mp 117–118.5 ℃.

【Shioiri T, Tet Lett1984, 25, 433】

相关文献

1 Pechman von H Chem Ber 1898 31 2950

2 Sheenan JC J Am Chem Soc 1949 71 4059

3 Matteson DS J Org Chem 1962 27 4293

4 Huisgen R Angew Chem 1963 75 604

5 Shioiri T Tet Lett 1984 25 433

6 Aoyama T Heterocycles 1988 27 343

7 Sandhu JS ARKIVOC 2007 xv 18

编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 367.

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