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Malononitrile dimer as a privileged reactant in design and skeletal diverse synthesis of heterocyclic motifs

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Abstract

Malononitrile dimer as a precursor reactant has been extensively applied in the diversity-oriented synthesis of various heterocyclic motifs, bis-heterocyclic compounds, fused heterocycle derivatives, bicyclic bridged heterocyclic scaffolds, and highly substituted carbocyclic compounds. These remarkable products were synthesized via various types of reactions, such as cycloaddition, cyclocondensation, cascade/domino/tandem reactions along with multi-component reactions. In addition, the flexibility and high reactivity of malononitrile dimer as a multi-functional reagent and its potential to the preparation of novel beneficial scaffolds as well as biologically active molecules signify it as a suitable building block in total synthesis, medicinal chemistry, and dyes. In the present review, the advances in the chemistry of malononitrile dimer as a potent reagent in organic synthesis have been reported in the past to now.

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Acknowledgements

We gratefully acknowledge financial support of the Iran National Elites Foundation (INEF) and the Research Council of Shahid Beheshti University and Catalyst Center of Excellence (CCE) at Shahid Beheshti University. We also thank Professor Guillermo A. Morales (Editor-in-Chief of Molecular Diversity) for his interesting comments, and Ph.D. students Reza Mohammadian and Mohammad Taghi Nazeri for redrawing some schemes.

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  1. Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani & Seyyed Emad Hooshmand

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  1. Ahmad Shaabani
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  2. Seyyed Emad Hooshmand
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Correspondence to Ahmad Shaabani.

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Shaabani, A., Hooshmand, S.E. Malononitrile dimer as a privileged reactant in design and skeletal diverse synthesis of heterocyclic motifs. Mol Divers 22, 207–224 (2018). https://doi.org/10.1007/s11030-017-9807-y

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