王爽, 吴沁, 林俊洁, 杨丽娟, 黄超. 微波辅助无催化剂绿色高效合成2,8-二氧双环[3.3.1]壬烷衍生物[J]. 云南大学学报(自然科学版), 2021, 43(5): 977-984. doi: 10.7540/j.ynu.20200659
引用本文: 王爽, 吴沁, 林俊洁, 杨丽娟, 黄超. 微波辅助无催化剂绿色高效合成2,8-二氧双环[3.3.1]壬烷衍生物[J]. 云南大学学报(自然科学版), 2021, 43(5): 977-984. doi: 10.7540/j.ynu.20200659
WANG Shuang, WU Qin, LIN Jun-jie, YANG Li-juan, HUANG Chao. Microwave irradiation catalyst-free green high efficiency synthesis of 2,8-dioxabicyclo[3.3.1]nonanes derivatives[J]. Journal of Yunnan University: Natural Sciences Edition, 2021, 43(5): 977-984. DOI: 10.7540/j.ynu.20200659
Citation: WANG Shuang, WU Qin, LIN Jun-jie, YANG Li-juan, HUANG Chao. Microwave irradiation catalyst-free green high efficiency synthesis of 2,8-dioxabicyclo[3.3.1]nonanes derivatives[J]. Journal of Yunnan University: Natural Sciences Edition, 2021, 43(5): 977-984. DOI: 10.7540/j.ynu.20200659

微波辅助无催化剂绿色高效合成2,8-二氧双环3.3.1壬烷衍生物

Microwave irradiation catalyst-free green high efficiency synthesis of 2,8-dioxabicyclo3.3.1nonanes derivatives

  • 摘要: 报道了一种微波辅助一锅绿色高效构筑复杂多环化合物—2,8-二氧双环3.3.1壬烷衍生物的方法. 以2-羟基查尔酮和2-羟基-1, 4-萘醌为原料, 在无催化剂微波辐射促进下,经迈克尔加成/脱水/分子内环化的串联过程, 以72%~89%高产率构筑了14个2,8-二氧双环3.3.1壬烷类化合物 (其中7个新化合物), 均经1H NMR、13C NMR、HRMS及IR表征鉴定. 该过程在40 min内即可完成, 一锅中形成2个C―C键和2个C―O键, 成键效率高, 且操作简洁, 后处理简单、无需柱层析分离产物, 只生成唯一的副产物水.

     

    Abstract: This paper reported a microwave-assisted synthetic method for efficiently constructing complex polycyclic compounds 2,8-dioxabicyclo 3.3.1 nonanes derivatives. Using 2-hydroxychalcone and 2-hydroxy-1, 4-naphquinone as raw materials, these compounds yield were 72%−89% through the tandem reaction of Michael addition/dehydration/intramolecular cyclization under the promotion of catalyst-free microwave radiation. Fourteen 2,8-dioxabicyclo 3.3.1 nonanes compounds (including seven new compounds) were constructed, all of which were characterized and identified by 1H NMR, 13C NMR, HRMS and IR. The efficient process can be completed within 40 minutes, the formation of 2 C―C bonds and 2 C―O bonds in one-pot, simple operation, simple post-processing, no column chromatography to separate products, and only by-product water is generated.

     

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