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Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A facile, convenient, and efficient synthesis of new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives has been accomplished via one-pot three-component reaction of 4-aminocoumarin, 1,3-dicarbonyl compounds (dimedone and Meldrum's acid), and substituted aromatic aldehydes in H2O or EtOH under reflux conditions using 10 mol % of guanidine hydrochloride as organocatalyst. Formation of products proceeds through tandem Knoevenagel and Michael reactions, followed by concomitant cyclization and dehydration or decarboxylation. A wide range of aromatic aldehydes were tolerated by the developed protocol. The advantages of this environmentally friendly synthetic approach are short reaction times, high atom economy, operational simplicity, application of readily available catalyst, z high yields of products, simple workup procedure, and possibility to purify products by recrystallization.

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The authors thank Research Council of the Payame Noor University for financial support.

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Authors and Affiliations

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

    Abolfazl Olyaei, Reyhaneh Mohammad Ebrahimi & Alireza Adl

  2. Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, Iran

    Mahdieh Sadeghpour

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  1. Abolfazl Olyaei
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  2. Reyhaneh Mohammad Ebrahimi
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  3. Alireza Adl
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  4. Mahdieh Sadeghpour
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Correspondence to Abolfazl Olyaei.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1104–1110

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Olyaei, A., Ebrahimi, R.M., Adl, A. et al. Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives. Chem Heterocycl Comp 55, 1104–1110 (2019). https://doi.org/10.1007/s10593-019-02585-4

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  • DOI: https://doi.org/10.1007/s10593-019-02585-4

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