Synthesis 2016; 48(09): 1253-1268
DOI: 10.1055/s-0035-1560413
review
© Georg Thieme Verlag Stuttgart · New York

Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds

Rajendra S. Rohokale
Department of Chemistry, Savitribai Phule Pune University (Formerly: University of Pune), Ganeshkhind, Pune-411007, India   eMail: uakshirsagar@chem.unipune.ac.in
,
Umesh A. Kshirsagar*
Department of Chemistry, Savitribai Phule Pune University (Formerly: University of Pune), Ganeshkhind, Pune-411007, India   eMail: uakshirsagar@chem.unipune.ac.in
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Publikationsverlauf

Received: 08. Dezember 2015

Accepted after revision: 28. Dezember 2015

Publikationsdatum:
09. März 2016 (online)


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