Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
Subrata Sahoo, Shantanu Pal
Abstract
A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
Topics & Concepts
NitrileHydrazine (antidepressant)ChemistryHydrateCatalysisHydrolysisSubstrate (aquarium)NitroCombinatorial chemistryCopperFunctional groupOrganic chemistryOne-pot synthesisReducing agentUreaOceanographyGeologyPolymerChromatographyAlkylQuinazolinone synthesis and applicationsPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Biological Evaluation