Synthesis of New Isoxazolidine Derivatives Utilizing the Functionality of <i>N</i>-Carbonylpyrazol-Linked Isoxazolidines
Xixian Cao,
Jun You,
Yunze Wang,
Yanchao Yu,
Wenju Wu,
Yifang Liang
Affiliations
Xixian Cao
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Jun You
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Yunze Wang
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Yanchao Yu
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Wenju Wu
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Yifang Liang
Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080, China
Using Ni(II) as the catalyst, electron-deficient 3,5-dimethylacryloylpyrazole olefin was reacted with C,N-diarylnitrones alone for 10 min to prepare novel five-member heterocyclic products, 4-3,5-dimethylacryloylpyrazole isoxazolidines with 100% regioselectivity and up to 99% yield. And then, taking these cycloadducts as substrates, six kinds of derivatization reactions, like ring-opening, nucleophilic substitution, addition-elimination and reduction, were studied. Experimental results showed that all kinds of transformations could obtain the target products at a high conversion rate under mild conditions, a finding which provided the basic methods for organic synthesis methodology research based on an isoxazolidine skeleton.
