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Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles

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Abstract

Eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives were obtained by the reaction of chiral (1R)-N-(1-phenylethyl)maleimide and C,N-aryl-substituted nitrilimines. The reaction afforded the cycloadducts as a regioisomeric mixture which can be separable in some cases. The structure and stereochemistry of cycloadducts were assigned on the basis of infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), mass and X-ray spectra, optical rotation measurements, and CHN analyses.

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Acknowledgments

Abant İzzet Baysal University, Directorate of Scientific Research Projects Unit (BAP grant 2007.03.03.260) and TÜBİTAK (The Scientific and Technological Research Council of Turkey, grant 106T645) are gratefully acknowledged for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Abant İzzet Baysal University, 14280, Bolu, Turkey

    Yaşar Dürüst & Muhammet Yıldırım

  2. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803-1804, USA

    Chris F. Fronczek & Frank R. Fronczek

Authors
  1. Yaşar Dürüst
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  2. Muhammet Yıldırım
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  3. Chris F. Fronczek
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  4. Frank R. Fronczek
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Correspondence to Yaşar Dürüst.

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Dürüst, Y., Yıldırım, M., Fronczek, C.F. et al. Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles. Monatsh Chem 143, 127–138 (2012). https://doi.org/10.1007/s00706-011-0618-z

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  • DOI: https://doi.org/10.1007/s00706-011-0618-z

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