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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进行了表征。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,Ⅲa的两个手性中心为(S,S)构型或者(R,R)构型。
7-azaindole as raw material, acylation and nitration to give 3-nitro-1-acyl-7-azaindole derivatives Ⅰa ~ g, then Ia ~ g and in situ generated 1,3 - dipole to dearomation [3 + 2] cycloaddition to give 7-azaindolino [3,4-b] tetrahydropyrrole derivatives (Ⅲa ~ g), and their synthesis conditions Optimized. The yields of Ⅲa ~ g ranged from 85% to 95% under the condition of dichloromethane as solvent and reaction at room temperature for 1 h. The diastereoselectivity dr> 99:1. The structure of the target compound was characterized by 1HNMR, 13CNMR and HR-MS. In addition, the target product (S, S) -6-benzyl-4b-nitro-8-toluenesulfonyl-4b, 5,6,7,7a, 8-hexahydropyrrolo [3 ’, 4’: 4,5] pyrrolo [2,3-b] pyridine (Ⅲa) were investigated by X-ray diffraction and the crystal structure was analyzed. The results showed that the two chiral centers of Ⅲa are (S, S) Or (R, R) configuration.