2,4-Diamino-5-(5-amino-3-oxo-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridine-3-carbonitrile

Abstract

The one-pot synthesis methodology has become the leading atom-economical approach for various chemical transformations in a single pot, without purifying intermediate compounds. Chromeno[2,3-b]pyridines are an important class of heterocyclic compounds with versatile biological profiles and other different applications The 5-aminopyrazole system represents a significant heterocyclic template that has gained considerable interest because of its long history of use in the pharmaceutical and agrochemical industries. In this communication, the one-pot transformation of salicylaldehyde, malononitrile dimer, and 2-cyanoacetohydrazide in an ethanol/pyridine mixture was investigated to provide 2,4-diamino-5-(5-amino-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile in good yield. The structure of the novel compound was confirmed by means of elemental analysis, mass-, nuclear magnetic resonance, and infrared spectroscopy.

Keywords

• one-pot process
• salicylaldehyde
• malononitrile dimer
• 2-cyanoacetohydrazide
• chromeno[2,3-<i>b</i>]pyridine