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Substrate-Switched Chemodivergent Pyrazole and Pyrazoline Synthesis: [3 + 2] Cycloaddition/Ring-Opening Rearrangement Reaction of Azadienes with Nitrile Imines. 2022
Liang Tu, and
Limei Gao, and
Qiang Wang, and
Zhixing Cao, and
Rong Huang, and
Yongsheng Zheng, and
Jikai Liu
School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China.
By virtue of a fundamentally new reaction model of benzofuran-derived azadienes (BDAs), an unprecedented synthesis of biologically important pyrazoles has been achieved through a tandem [3 + 2] cycloaddition/ring-opening rearrangement reaction of BDAs with nitrile imines. The nature and type of substrates are found to act as a chemical switch to trigger two distinct reaction pathways. A minor modification to the substrates allows the access to spiro-pyrazolines.
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