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以2,3-吡啶二羧酸作为起始原料,通过环合、氢化及内酰胺还原反应合成标题化合物,作为合成莫西沙星侧链(S,S)-2,8-二氮杂双环[4.3.0]壬烷的新型中间体。对各个中间体制备过程中原料的用量比进行了探究:在2,3-吡啶二酸酐的制备中,2,3-吡啶二羧酸与SOCl2的物质的量比为1∶1.35;在6-(1-苯基-乙基)-吡咯并[3,4-b]吡啶-5,7-二酮的制备中,2,3-吡啶二酸酐与SOCl2的物质的量比为n(2,3-吡啶二酸酐)∶n(SOCl2)=1∶1.10;在目标产物的制备中,n(6-(1-苯基-乙基)-6H-吡咯并[3,4-b]吡啶-5,7-二酮)∶n(Na BH4)∶n(BF3·Et2O)=1∶3.2∶3.2×0.95。另外,在氢化还原反应中,选用冰醋酸作为反应溶剂,目标化合物总收率73.7%,并通过1HNMR对中间体及产物结构进行了确证。该研究为(S,S)-2,8-二氮杂双环[4.3.0]壬烷的合成提供了新思路。
The title compound was synthesized by cyclisation, hydrogenation and lactam reduction using 2,3-pyridinedicarboxylic acid as a starting material for the synthesis of the moxifloxacin side chain (S, S) -2,8-diazabicyclo [ 4.3.0] nonane new intermediate. In the preparation of 2,3-pyridine dianhydride, the amount ratio of 2,3-pyridinedicarboxylic acid to SOCl2 was 1: 1.35; (1-phenyl-ethyl) -pyrrolo [3,4-b] pyridine-5,7-dione, the amount ratio of 2,3-pyridine dianhydride to SOCl2 is n (2, (1-phenyl-ethyl) -6H-pyrrolo [3,4-b] pyridine- 5,7-dione): n (Na BH4): n (BF3Et2O) = 1: 3.2: 3.2 × 0.95. In addition, in the hydrogenation reduction reaction, glacial acetic acid was selected as the reaction solvent, the total yield of the target compound was 73.7%, and the intermediates and the product structure were confirmed by 1HNMR. This study provides a new idea for the synthesis of (S, S) -2,8-diazabicyclo [4.3.0] nonane.