Chinese Journal of Organic Chemistry >
N-Heterocyclic Carbene-Catalyzed [4＋2] Cycloaddition of Salicylaldehydes with Pyrazole-4,5-diones for the Synthesis of Spiroketal-Pyrazolones
Received date: 2024-06-04
Revised date: 2024-07-10
Online published: 2024-08-26
Supported by
Shihezi University(2022ZK003); Shihezi University(RCZK202001); Tianchi Talent Project of Xinjiang Uygur Autonomous Region(CZ002737)
The first efficiently N-heterocyclic carbene-catalyzed [4＋2] cycloaddition of salicylaldehydes and pyrazole-4,5- diones to directly synthesis of spiro-ketal-pyrazolones bearing both oxygens of the ketal unit in the same ring was disclosed. This reaction was qualified with broad substrate scope, achieving moderate to excellent yield (up to 98%). This method has mild reaction conditions and simple operation, providing a new attractive strategy for the practical syntheses of multi- functionalized spiroketals including pyrazolone structures with mild reaction condition and operational simplicity. Furthermore, the gram scale and derivative transformations have also been achieved.
Xiaomei Wang , Yan Liu , Shiwu Li , Zhifei Zhao . N-Heterocyclic Carbene-Catalyzed [4＋2] Cycloaddition of Salicylaldehydes with Pyrazole-4,5-diones for the Synthesis of Spiroketal-Pyrazolones[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 267 -275 . DOI: 10.6023/cjoc202406005
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