4.5 Article

DBU-Promoted Three-Component Cascade Annulations to Access Multiply Substituted 3-Cyano-thiophenes

期刊

ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 11, 期 10, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200394

关键词

cascade annulation; metal-free; multiply substituted 3-cyano-thiophenes; three-component reaction

资金

  1. National Natural Science Foundation of China [21867001, 22167002, 21662002, 21602031]
  2. Academic & Technical Leadership Development Program of Jiangxi Province [20194BCJ22014]
  3. Double-Thousand Talents Plan of Jiangxi Province [jxsq2019201025]
  4. Jiangxi Provincial Natural Science Foundation [20202ACBL206022, 20171BAB203010]
  5. Science Foundation of Jiangxi Provincial Department of Education [GJJ201429]

向作者/读者索取更多资源

The metal-free [2+2+1] three-component cascade annulations described in this study allow for the efficient synthesis of multiply substituted 3-cyano-thiophenes with good functional group tolerance and simple reaction conditions, showing potential applications in medicinal chemistry through late-stage modifications of structurally complex bioactive molecules and drugs.
Metal-free [2+2+1] three-component cascade annulations for the one-pot synthesis of multiply substituted 3-cyano-thiophenes from 3-oxo-nitriles, enones and elemental sulfur are described. This DBU-promoted protocol features good functional group tolerance, and provides high value 3-cyano-thiophenes in moderate to good yields under simple reaction conditions. This approach also enables late-stage modifications of structurally complex bioactive molecules and drugs, which exhibits potential applications in medicinal chemistry.

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