4.8 Article

Synthesis of o-Carborane-Fused Pyrazoles through Sequential C-N Bond Formation

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ORGANIC LETTERS
卷 24, 期 19, 页码 3526-3531

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01232

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资金

  1. National Research Foundation of Korea (NRF) - Korean government [2021R1A2C3008862]
  2. National Research Foundation of Korea [2021R1A2C3008862] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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A transition-metal-free synthetic method for o-carborane-fused pyrazoles has been developed, allowing twofold C-N bond formation under extremely mild conditions and high functional group tolerance. This method involves sequential diazotization and cyclization reactions in one pot using B(4)-acylmethyl or B(3,5)-diacylmethyl o-carborane and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) in the presence of DBU in acetonitrile.
Transition-metal-free synthetic method for o-carborane-fused pyrazoles as a new scaffold has been developed from the reaction of B(4)-acylmethyl or B(3,5)-diacylmethyl o-carborane with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) in the presence of DBU in acetonitrile through sequential diazotization and cyclization reaction in one pot, consequently allowing twofold C-N bond formation under extremely mild conditions and high functional group tolerance.

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