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Synthesis of new unsymmetrical imidazolinium salts with mesityl and nitrophenyl substituents

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Abstract

An efficient five-step procedure for synthesis of unsymmetrical imidazolinium salts with mesityl and nitrophenyl substituents was elaborated. The starting nitroaniline was acylated with chloroacetyl chloride followed by Finkelstein displacement by iodide and coupling with mesitylamine. The key step was reduction of the amide carbonyl group with BH3·S(CH3)2. Finally, an imidazoline ring was constructed by reaction with trimethyl orthoformate. A different approach was attempted for 2,6-dinitroaniline, but final cyclization failed in this case.

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Acknowledgments

Financial support from the Polish National Science Centre (DEC-2011/02/A/ST5/00459) is gratefully acknowledged.

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Authors and Affiliations

  1. Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399, Białystok, Poland

    Marta Malinowska, Agnieszka Hryniewicka, Stanisław Witkowski & Jacek W. Morzycki

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  1. Marta Malinowska
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  2. Agnieszka Hryniewicka
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  3. Stanisław Witkowski
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  4. Jacek W. Morzycki
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Correspondence to Marta Malinowska.

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Malinowska, M., Hryniewicka, A., Witkowski, S. et al. Synthesis of new unsymmetrical imidazolinium salts with mesityl and nitrophenyl substituents. Monatsh Chem 145, 1653–1661 (2014). https://doi.org/10.1007/s00706-014-1248-z

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  • DOI: https://doi.org/10.1007/s00706-014-1248-z

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