GREEN SYNTHETIC APPROACH TOWARD NEW CHROMENO[4,3-<i>b</i>]QUINOLINE AND CHROMENO[4,3-<i>b</i>]PYRIDINE DERIVATIVES

Authors

  • Abolfazl Olyaei Department of Chemistry, Payame Noor University, P. O. Box 19395-4697, Tehran, Iran
  • Reyhaneh Mohammad Ebrahimi Department of Chemistry, Payame Noor University, P. O. Box 19395-4697, Tehran, Iran
  • Alireza Adl Department of Chemistry, Payame Noor University, P. O. Box 19395-4697, Tehran, Iran
  • Mahdieh Sadeghpour Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, Iran

DOI:

https://doi.org/10.1007/5227

Keywords:

4-aminocoumarin, chromeno[4, 3-b]pyridine, 3-b]quinoline, guanidine hydrochloride.

Abstract

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, high yields of products, simple workup procedure, and possibility to purify products by recrystallization.

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Published

2019-11-13

Issue

Vol. 55 No. 11 (2019)

Section

Original Papers