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Rapid synthesis of 2-amino maleonitrile Schiff bases in aqueous media catalyzed by cerium(IV) ammonium nitrate (CAN) and a new method for the one-pot preparation of their dicyano imidazoles (DCI)

Research on Chemical Intermediates volume 43, pages 3349–3360 (2017)Cite this article

Abstract

A quick and simple method has been developed for the synthesis of 2-amino maleonitrile Schiff bases 3(a–k) through the reaction of 2,3-diaminomaleonitrile (DAMN) and aromatic aldehydes in the presence of catalytic amounts of cerium(IV) ammonium nitrate (CAN) in aqueous media at room temperature. Also, the facile synthesis of 2-aryl-4,5-dicarbonitrile imidazoles 4(a–k) by one-pot condensation of DAMN with various aromatic aldehydes using CAN as efficient reagent in acetonitrile at 50 °C has been described. In this way, the one-pot synthesis of raw materials is presented for the first time. The new synthesized compounds were characterized using IR, 1H NMR, 13C NMR and mass spectroscopy. The present procedure offers several advantages, such as good to excellent yields, the use of an inexpensive and available catalyst, easy and quick isolation of the pure product and short reaction times compared with previous reports.

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Acknowledgement

We are grateful to the research commute of Chemistry Department of Payame Noor University for providing of financial and technical supports of this work.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, Tehran, 19395-4697, Iran

    Mehdi Kalhor & Zahra Seyedzade

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  1. Mehdi Kalhor
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  2. Zahra Seyedzade
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Correspondence to Mehdi Kalhor.

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Kalhor, M., Seyedzade, Z. Rapid synthesis of 2-amino maleonitrile Schiff bases in aqueous media catalyzed by cerium(IV) ammonium nitrate (CAN) and a new method for the one-pot preparation of their dicyano imidazoles (DCI). Res Chem Intermed 43, 3349–3360 (2017). https://doi.org/10.1007/s11164-016-2829-8

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  • DOI: https://doi.org/10.1007/s11164-016-2829-8

Keywords

  • DAMN
  • Catalyst
  • CAN
  • Aqueous media
  • Schiff base
  • One-pot synthesis
  • Dicyano imidazole