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Dual 1,3-dipolar cycloaddition of nitrilimines with cyclopenta[a]acenaphthylen-8-ones. A synthesis of hexacyclic bis-dihydropyrazoles

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Abstract

A regioselective 1,3-dipolar cycloaddition of nitrilimines, generated from hydrazonoyl chlorides, with both C = C double bonds of cyclopentadienone moiety of cyclopenta[a]acenaphthylen-8-ones in the presence of Et3N is described. This dual cycloaddition reaction affords a nearly 3:2 mixture of symmetrical and unsymmetrical hexacyclic bis-dihydropyrazol derivatives in good yields. The stereochemistry of diethyl 3,7-bis(4-chlorophenyl)-4-oxo-1,5-diphenyl-1H-naphtho[1′,8′:4,5,6]pentaleno[1,6a-c:3a,3-c′]dipyrazole-3a,4a(4H,5H)-dicarboxylate was established by X-ray crystallography.

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Acknowledgements

We thank the Research Council of Tarbiat Modares University for supporting this work

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, 175, PO Box 14115, Tehran, Iran

    Issa Yavari, Parisa Ravaghi & Maryam Safaei

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  1. Issa Yavari
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  2. Parisa Ravaghi
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  3. Maryam Safaei
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Correspondence to Issa Yavari.

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Yavari, I., Ravaghi, P. & Safaei, M. Dual 1,3-dipolar cycloaddition of nitrilimines with cyclopenta[a]acenaphthylen-8-ones. A synthesis of hexacyclic bis-dihydropyrazoles. Monatsh Chem 151, 1121–1129 (2020). https://doi.org/10.1007/s00706-020-02638-x

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  • DOI: https://doi.org/10.1007/s00706-020-02638-x

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