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Benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines: synthesis, mechanistic studies, and crystal structure determination

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Abstract

New benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines are prepared in the reaction of o-phthalaldehyde and substituted 2-aminobenzothiazoles and 2-aminobenzimidazoles. The optimization of these reactions is discussed, and the reaction mechanisms are proposed based on the experimental findings. Isoindolines with other heterocyclic substituents are prepared as a confirmation of the proposed mechanisms. Molecular and crystal structures of several prepared compounds are determined by a single crystal X-ray diffraction. These structures are found to be in line with projections based on the chemical and spectroscopic properties, and thus offer an additional confirmation of the proposed reaction mechanisms.

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Acknowledgments

This work was financially supported by Croatian Science Foundation (project No. 5596).

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Zagreb, Croatia

    Irena Sović, Iva Orehovec & Grace Karminski-Zamola

  2. Department of Chemistry, Faculty of Science, University of Zagreb, Zagreb, Croatia

    Vladimir Stilinović

  3. Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia

    Nikola Basarić

Authors
  1. Irena Sović
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  2. Iva Orehovec
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  3. Vladimir Stilinović
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  4. Nikola Basarić
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  5. Grace Karminski-Zamola
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Corresponding authors

Correspondence to Irena Sović or Grace Karminski-Zamola.

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Sović, I., Orehovec, I., Stilinović, V. et al. Benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines: synthesis, mechanistic studies, and crystal structure determination. Monatsh Chem 147, 1825–1837 (2016). https://doi.org/10.1007/s00706-016-1796-5

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  • DOI: https://doi.org/10.1007/s00706-016-1796-5

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