A Convenient Method for the Synthesis of Chromeno[4,3-b]pyridines Via Three-component Reaction

Author(s): Hamideh Nikookar, Setareh Moghimi, Mohammad Hosein Sayahi, Mohammad Mahdavi, Parviz Rashidi Ranjbar*, Loghman Firoozpour, Alireza Foroumadi*

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 21 , Issue 5 , 2018

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Aim and Objective: The importance of Chromeno[4,3-b]pyridines in bioactive compounds, highlighted the ongoing research on developing novel methods for the construction of this heterocyclic scaffold. Regarding the advantageous features of multi-component reactions in organic synthesis, we will try to synthesize pyridocoumarins through this method.

Materials and Methods: Chromeno[4,3-b]pyridines were conveniently prepared from a threecomponent condensation reaction between 4-hydroxy coumarin, ammonia and ethyl 2,4-dioxo-4- arylbutanoates in refluxing n-propanol. The synthesized compounds were characterized by NMR, IR and Mass spectroscopy.

Results: The reaction proceeded through an in situ formed 4-amino coumarin, affording eight new target compounds in good yields.

Conclusion: This method introduce a novel approach to ethyl 4-aryl-5-oxo-5H-chromeno[4,3- b]pyridine-2-carboxylate derivatives and allow organic chemists to prepare 4-aminocoumarin in reaction medium.

Keywords: Pyridocoumarin, multi-component reaction, 4-amino coumarin, one-pot, 4-hydroxy coumarin, ammonia.

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Article Details

Year: 2018
Published on: 20 July, 2018
Page: [344 - 348]
Pages: 5
DOI: 10.2174/1386207321666180524110635
Price: $65

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