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Synthesis of functionalized dispiro[indoline-3,1\({^{\prime }}\)-cyclopentane-3\({^{\prime }}\),3\({^{\prime \prime }}\)-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoylhydrazides and arylhydrazines

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Abstract

The triethylamine-promoted domino cyclodimerization reaction of 3-phenacylideneoxindolines with benzohydrazides in acetonitrile afforded densely substituted dispiro[indoline-3,1\({^{\prime }}\)-cyclopentane-3\({^{\prime }}\),3\({^{\prime \prime }}\)-indolines] in good yields and with high diastereoselectivity. The similar domino reaction of 3-phenacylideneoxindoles with arylhydrazines also gave corresponding dispiro[indoline-3,1\({^{\prime }}\)-cyclopentane-3\({^{\prime }}\),3\({^{\prime \prime }}\)-indolines] with hydrazinyl or arylazo groups according to the structures of arylhydrazines.

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Acknowledgements

This work was financially supported by National Natural Science Foundation of China (Grant No. 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We thank Analysis and Test Center of Yangzhou University for providing all analytical instruments.

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  1. College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

    Ren-Yin Yang, Jing Sun, Gong Jin & Chao-Guo Yan

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Yang, RY., Sun, J., Jin, G. et al. Synthesis of functionalized dispiro[indoline-3,1\({^{\prime }}\)-cyclopentane-3\({^{\prime }}\),3\({^{\prime \prime }}\)-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoylhydrazides and arylhydrazines. Mol Divers 22, 21–36 (2018). https://doi.org/10.1007/s11030-017-9786-z

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