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Current progress in asymmetric Biginelli reaction: an update

Molecular Diversity volume 22, pages 751–767 (2018)Cite this article

Abstract

The Biginelli reaction, involving a three-component reaction of an aromatic aldehyde, urea and ethyl acetoacetate, has emerged as an extremely useful synthetic tool to organic chemists for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones and related heterocyclic compounds. In the past decades, the asymmetric variants of this reaction have been at the forefront of investigations in several research groups. In 2013, we highlighted the developments occurred in the asymmetric version of the Biginelli reaction. This review article focuses on the recent developments of asymmetric Biginelli reaction covers the literature going back to 2012.

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Abbreviations

DCC:

N,N′-Dicyclohexylmethandiimine

DCM:

Dichloromethane

DIPEA:

Diisopropylethylamine

DMEDA:

Dimethylethylenediamine

TBTU:

2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

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Acknowledgements

We are grateful for financial support from the Research Council of Alzahra University. MMH is also appreciate the financial support granted by Iran National Science Foundation (INSF) under the given individual research chair.

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Authors and Affiliations

  1. Department of Chemistry, Alzahra University, Tehran, Iran

    Majid M. Heravi, Razieh Moradi & Leyla Mohammadkhani

  2. Department of Chemistry, Razi University, Kermanshah, 67149, Iran

    Borzou Moradi

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  1. Majid M. Heravi
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  2. Razieh Moradi
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  3. Leyla Mohammadkhani
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  4. Borzou Moradi
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Correspondence to Majid M. Heravi.

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Heravi, M.M., Moradi, R., Mohammadkhani, L. et al. Current progress in asymmetric Biginelli reaction: an update. Mol Divers 22, 751–767 (2018). https://doi.org/10.1007/s11030-018-9841-4

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Keywords

  • Biginelli reaction
  • 3-4-Dihydropyrimidine-2-(1H)-ones
  • Heterocyclic compounds
  • Asymmetric reaction
  • Enantioselective reaction
  • Catalysis
  • Pyrimidines
  • Enantioselectivity
  • Stereoselectivity
  • MCRs