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Homoallenyl azines in criss-cross cycloaddition reactions

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Abstract

Thermally initiated combined intra-intermolecular criss-cross cycloadditions of substituted nonsymmetrical allenyl azines with isocyanate or isothiocyanate dipolarophiles were investigated. Substituted 1,3,10-triazatricyclo[5.2.1.04,10]dec-6-en-2-ones or -dec-6-ene-2-thiones were obtained as the main products in moderate to very good yields. The thermal stabilities of the tricyclic adducts in reactions with the competing reactive dipolarophile dimethyl acetylenedicarboxylate were studied and are discussed. In some cases, substituted 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles were found as side products. This reaction showed high atom economy and in all cases we observed the presence of one diastereoisomer and regioisomer only, which was clearly revealed by crystallographic analysis.

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Acknowledgments

The research was supported by the Grant Agency of the Czech Republic, grant no. 203/09/1345. We are grateful to Marek Nečas for crystallographic measurements and to Lukáš Maier for NMR measurements on the Bruker Avance 500.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37, Brno, Czech Republic

    Juraj Galeta, Stanislav Man, Aneta Valoušková & Milan Potáček

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  1. Juraj Galeta
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  2. Stanislav Man
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  3. Aneta Valoušková
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  4. Milan Potáček
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Correspondence to Milan Potáček.

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Galeta, J., Man, S., Valoušková, A. et al. Homoallenyl azines in criss-cross cycloaddition reactions. Monatsh Chem 144, 205–216 (2013). https://doi.org/10.1007/s00706-012-0865-7

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  • DOI: https://doi.org/10.1007/s00706-012-0865-7

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