Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3- b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism

Molecules. 2020 May 31;25(11):2573. doi: 10.3390/molecules25112573.

Abstract

The Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for the synthesis of previously unknown hydroxyquinolinone substituted chromeno[2,3-b]pyridines via reaction of salicylaldehydes, malononitrile dimer and hydroxyquinolinone. It was shown that an ethanol-pyridine combination is more beneficial than other inorganic or organic catalysts. Quantum chemical studies showed that chromeno[2,3-b]pyridines has potential for corrosion inhibition. Real time 1H NMR monitoring was used for the investigation of reaction mechanism and 2-((2H-chromen-3-yl)methylene)malononitrile was defined as a key intermediate in the reaction.

Keywords: NMR monitoring; PASE approach; chromeno[2,3‑b]pyridines; corrosion inhibitor; hydroxyquinolinone; malononitrile dimer; multicomponent reactions; salicylaldehyde.

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Dimerization
  • Ethanol / chemistry
  • Hydroxyquinolines / chemistry
  • Magnetic Resonance Spectroscopy
  • Nitriles / chemistry
  • Pyridines / chemistry*
  • Quantum Theory
  • Quinolones / chemistry*
  • Solvents / chemistry*

Substances

  • Aldehydes
  • Hydroxyquinolines
  • Nitriles
  • Pyridines
  • Quinolones
  • Solvents
  • salicylaldehyde
  • Ethanol
  • dicyanmethane
  • pyridine