7-氮杂吲哚去芳香化[3+2]环加成合成7-氮杂吲哚啉并[3,4-b]四氢吡咯骨架衍生物
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Dearomatization of 7-Azaindole Synthesis of Pyrrolo[3,4-b]-7-azaindole Derivatives through [3+2] Dipolar Cycloaddition
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    摘要:

    以7-氮杂吲哚为原料,经酰化和硝化得到3-硝基-1-酰基-7-氮杂吲哚衍生物Ⅰa~g,再由Ⅰa~g和原位产生的1,3-偶极子发生去芳香化[3+2]环加成反应得到7-氮杂吲哚啉并[3,4-b]四氢吡咯衍生物(Ⅲa~g),并对其合成条件进行了优化,在二氯甲烷作溶剂,室温反应1 h的条件下,Ⅲa~g的产率为85%~95%,非对映选择性dr>99:1。目标化合物的结构经1HNMR、13CNMR和HR-MS进行表征,确认合成了目标产物。此外,对目标产物(S,S)-6-苄基-4b-硝基-8-甲苯磺酰基-4b,5,6,7,7a,8-六氢吡咯并[3',4':4,5]吡咯并[2,3-b]吡啶(Ⅲa)进行了X射线衍射测试,对其晶体结构进行了分析,结果表明,化合物Ⅲa的两个手性中心为(S,S)构型或者(R,R)构型。

    Abstract:

    Hexahydropyrrolo[3,4-b]-7-azaindole derivatives were synthesized from 3-nitroazaindoles and 1,3-dipole which was generated in situ through [3+2] dipolar cycloaddition. The synthetic conditions of hexahydropyrrolo[3,4-b]-7-azaindole derivatives were optimized, using methylene chloride as solvent, and with the reaction taking place at room temperature for 1 h. The yield under such conditions was 85%~95% and the diastereoselectivity was over 99:1. The structures of these compounds were characterized by 1H-NMR, 13C-NMR and high resolution mass spectrometry analysis. The results showed that target structures products were obtained. Furthermore, X-ray diffraction was used to analysis the structures of compound (S,S)-6-benzyl-4b-nitro-8-tosyl-4b,5,6,7,7a,8-hexahydropyrrolo[3',4':4,5]pyrrolo[2,3-b]pyridine (Ⅲa). The result showed that the relative configuration of chiral center was (S,S) or (R,R).

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王凯凯,邓金根.7-氮杂吲哚去芳香化[3+2]环加成合成7-氮杂吲哚啉并[3,4-b]四氢吡咯骨架衍生物[J].精细化工,2016,33(9):

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  • 收稿日期:2016-04-23
  • 最后修改日期:2016-05-26
  • 录用日期:2016-06-07
  • 在线发布日期: 2016-08-17
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