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

[ Vol. 21 , Issue. 5 ]

Author(s):

Hamideh Nikookar, Setareh Moghimi, Mohammad Hosein Sayahi, Mohammad Mahdavi, Parviz Rashidi Ranjbar*, Loghman Firoozpour and Alireza Foroumadi*   Pages 344 - 348 ( 5 )

Abstract:


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.

Affiliation:

School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, The Institute of Pharmaceutical Sciences (TIPS) and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, The Institute of Pharmaceutical Sciences (TIPS) and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, The Institute of Pharmaceutical Sciences (TIPS) and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran



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