Truce-Smiles Rearrangement Cascade Enables Synthesis of Pyrazoline Derivatives
Dengyuan Gao1, Jiacheng Deng2, Zhenguang Guo1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, P. R. China.
None:
A five-bond-forming cascade reaction for synthesizing pyrazoline derivatives is described. The transformation involves N-(arylsulfonyl) acrylamides and in situ generated Huisgen zwitterions from azodicarboxylates and triphenylphosphine under mild, base-free conditions. A conjugate addition-Smiles rearrangement-cyclization sequence affords diverse pyrazolines in moderate to excellent yields. This work represents the first incorporation of Huisgen zwitterions into a Truce-Smiles cascade, enabling unprecedented five-bond construction in one step with demonstrated scalability and structural diversification.
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