I2-promoted formal [3+1+1+1] cyclization to construct 5-cyano-1H-pyrazolo[3,4-b]pyridine using malononitrile as a C1 synthon

作者：Yu, Zhi-Cheng; Shen, Xi; Zhou, You; Chen, Xiang-Long; Wang, Li-Sheng; Wu, Yan-Dong; Zhang, Hao-Ke; Zheng, Kai-Lu^*; Wu, An-Xin^*

来源：Organic Chemistry Frontiers, 2023, 10(23): 5958-5964.

DOI：10.1039/d3qo01299a

• ONE-POT
• CATALYST-FREE
• ONE-STEP
• REDUCTIVE DECYANATION
• EFFICIENT SYNTHESIS
• DOMINO STRATEGY
• VISIBLE-LIGHT
• DERIVATIVES
• METHYL

A novel [3 + 1 + 1 + 1] cyclization reaction for the synthesis of compounds based on a 5-cyano-1H-pyrazolo[3,4-b]pyridine skeleton from aryl methyl ketones, malononitrile and 5-aminopyrazoles has been established. This I-2-meditated process allows direct cleavage of the C-C bond of malononitrile to generate a C1 synthon and the construction of three C-C bonds and one C-N bond in a one-pot system. This method is facile and compatible with a wide range of substrates. Significantly, some products exhibit good aggregation-induced emission (AIE) characteristics without any further modification.

• 单位
  1; 广东医学院