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1,3-Dipolar cycloaddition of diphenylnitrilimine and 5-arylmethylidene-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones to afford novel spiro[indazole-5,3′-pyrazole] derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Novel 4'-aryl-1,2',5'-triphenyl-2',4',6,7-tetrahydrospiro[indazole-5,3'-pyrazol]-4(1H)-ones have been synthesized in moderate yields by 1,3-dipolar cycloaddition of 5-arylmethylidene-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones and diphenylnitrilimine, generated in situ from N-phenylbenzohydrazonoyl chloride and triethylamine. According to structural analyses by NMR spectroscopy and single crystal X-ray diffraction method, the reaction proceeds regioselectively affording products with C(5)–C(3') connectivity at the spiro center.

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Authors and Affiliations

  1. Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, Hunan, China

    Demin Ren, Guoqiang Kuang & Xiaofang Li

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  1. Demin Ren
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  2. Guoqiang Kuang
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  3. Xiaofang Li
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Correspondence to Xiaofang Li.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1117–1120

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Ren, D., Kuang, G. & Li, X. 1,3-Dipolar cycloaddition of diphenylnitrilimine and 5-arylmethylidene-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones to afford novel spiro[indazole-5,3′-pyrazole] derivatives. Chem Heterocycl Comp 54, 1117–1120 (2018). https://doi.org/10.1007/s10593-019-02401-z

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