Abstract

2,3-Dihydroquinazolin-4-one (DHQ) belongs to the class of nitrogen-containing heterocyclic compounds representing a core structural component in various biologically active compounds. In the past decades, several methodologies have been developed for the synthesis of the DHQ framework, especially the 2-substituted derivatives. Unfortunately, multistep syntheses, harsh reaction conditions, and the use of toxic reagents and solvents have limited their full potential as a versatile fragment. Recently, use of green chemistry and alternative strategies are being explored to prepare diverse DHQ derivatives. This fragment is used as a synthon for the preparation of biologically active quinazolinones and as a functional substrate for the synthesis of modified DHQ derivatives exhibiting different biological properties. In this review, we provide a comprehensive assessment of the synthesis and biological evaluations of DHQ derivatives.

Highlights

  • View Article Online2,3-Dihydroquinazolin-4-one (DHQ) belongs to the class of nitrogen-containing heterocyclic compounds representing a core structural component in various biologically active compounds

  • Nitrogen-containing heterocyclic scaffolds are quite common fragments in drugs and biologically active compounds.[1,2] The 2,3-dihydroquinazolin-4(1H)-one (DHQ) is an important aDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, Ed

  • Some asymmetric strategies have been attempted, the aminal chiral center is sensitive to racemization, making it difficult to Mariateresa Badolato is currently pursuing her PhD degree in Translational Medicine under the supervision of Dr Francesca Aiello and Professor Antonio Garofalo at the University of Calabria, Italy

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Summary

View Article Online

2,3-Dihydroquinazolin-4-one (DHQ) belongs to the class of nitrogen-containing heterocyclic compounds representing a core structural component in various biologically active compounds. Several methodologies have been developed for the synthesis of the DHQ framework, especially the 2substituted derivatives. Multistep syntheses, harsh reaction conditions, and the use of toxic reagents and solvents have limited their full potential as a versatile fragment. Use of green chemistry and alternative strategies are being explored to prepare diverse DHQ derivatives. This fragment is used as a synthon for the preparation of biologically active quinazolinones and as a functional substrate for the synthesis of modified DHQ derivatives exhibiting different biological properties. We provide a comprehensive assessment of the synthesis and biological evaluations of DHQ derivatives

Introduction
Basic catalysis
Acid catalysis
Iodine and metal salts as catalysts
Ammonium salt
Intramolecular cyclization of a Schiff base
Schiff base
Conventional reaction conditions
Solid acidic Catalyst
Heterogeneous and reusable catalysts
Greener and convenient approaches to obtain DHQ derivatives
Nature catalyst Recyclable Solid acid
Alternative solvents
Hydrotropic solution Deep eutectic solvent
Aldehyde Aldehyde Amine
Other strategies
Enantioselective synthesis of DHQ derivatives
DHQ as an intermediate in organic chemistry
DHQ as a versatile fragment in drug design
Antimalarial Antiviral
Findings
Conclusions
Full Text
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