Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds

Abstract

Quinazolinones are important heterocyclic scaffolds because of their broad spectrum of medicinal and pharmacological properties. The development of advanced synthetic methods to construct the quinazolinone motif is therefore an important aspect of synthetic chemistry. This review emphasises the recent developments in methodologies and advanced synthetic strategies for the quinazolinone core.

1 Introduction

2 Synthesis of 2-Substituted Quinazolinones

2.1 Oxidative Condensation/Cyclization

2.2 Acid-Catalyzed Condensation/Cyclization

2.3 Transition-Metal-Catalyzed C–N Bond Formation

2.4 Transition-Metal-Catalyzed Cyclocarbonylation

3 Synthesis of 3-Substituted Quinazolinones

3.1 Using a Coupling Agent

3.2 Oxidative Condensation/Cyclization

3.3 Transition-Metal-Catalyzed C–N Bond Formation

3.4 Transition-Metal-Catalyzed Cyclocarbonylation

4 Synthesis of 2,3-Disubstituted Quinazolinones

4.1 Dehydrative/Reductive Cyclization

4.2 Oxidative Condensation/Cyclization

4.3 Radical Cyclization

4.4 Transition-Metal-Catalyzed C–N Bond Formation

4.5 Transition-Metal-Catalyzed Cyclocarbonylation

4.6 Acid-Catalyzed Condensation/Cyclization

5 Conclusion

Key words

quinazolinone - synthesis - heterocycles - oxidative coupling - radical - cascade cyclization

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