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Synthesis of 1,2-dihydroacridines based on chloroquinoline-3-carbaldehyde and diketene under catalyst-free reaction

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Abstract

A green, facile, and efficient method for the synthesis of novel 1,2-dihydroacridine-2-carboxamide derivatives was effectively performed via a one-pot pseudo-five component cascade reaction involving 2-chloroquinoline-3-carbaldehyde, 1-phenyl-2-(triphenylphosphoranylidene)ethanone, diketene, and several primary amines in ethanol at 70 °C, in one pot reaction. This novel effective cascade reaction was accomplished probably via a sequence of Wittig reaction/SN reaction/Michael addition/intramolecular C-cyclization and imine hydrolysis. The advantages of this method are operational simplicity, atom economy, short reaction times, facile work-up procedure, and very high yields.

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Acknowledgements

The authors appreciate partial financial supports from Alzahra University.

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Authors and Affiliations

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

    Atieh Rezvanian, Farzaneh Noorakhtar, Vahideh Zadsirjan & Majid. M. Heravi

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  1. Atieh Rezvanian
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  2. Farzaneh Noorakhtar
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  3. Vahideh Zadsirjan
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  4. Majid. M. Heravi
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Correspondence to Atieh Rezvanian.

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Rezvanian, A., Noorakhtar, F., Zadsirjan, V. et al. Synthesis of 1,2-dihydroacridines based on chloroquinoline-3-carbaldehyde and diketene under catalyst-free reaction. Monatsh Chem 154, 651–659 (2023). https://doi.org/10.1007/s00706-023-03064-5

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  • DOI: https://doi.org/10.1007/s00706-023-03064-5

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