Recent Advances on the Development of Synthetic Strategies to Access Dibenzoxepine Derivatives

Abstract

Dibenzoxepines have gained privileged status in medicinal chemistry and drug discovery due to their appearance in various natural products and life-saving drug molecules. Dibenzoxepine-based molecules, such as artocarpols, asenapine, and pacharin, possess a wide range of biological activities including anti-inflammatory, antidepressant, antihypertensive, antiestrogenic, and insecticidal activities. Therefore, designing and developing new methodologies to access the dibenzoxepine­ core has become a paramount research topic for organic/ medicinal chemists. Herein, we reviewed various synthetic methods to access dibenzoxepine derivatives. The total syntheses of dibenzoxepine-based natural products and biologically/medicinally important molecules have also been reviewed.

1 Introduction

2 Transition-Metal-Free Approaches

2.1 Acid-Mediated Transformations

2.2 Base-Mediated Transformations

2.3 NHC-Organocatalyzed Transformations

2.4 Miscellaneous

3 Metal-Mediated Approaches

4 Transition-Metal-Catalyzed Approaches

4.1 Iron-Catalyzed Transformations

4.2 Copper-Catalyzed Transformations

4.3 Ruthenium-Catalyzed Transformations

4.4 Palladium-Catalyzed Transformations

4.5 Other Transition-Metal-Catalyzed Transformations

5 Total Syntheses

6 Conclusion

Key words

dibenzoxepine - NHC organocatalysis - transition-metal catalysis - S_NAr reaction - natural products - active pharmaceutical ingredients (APIs)

Publication History

Received: 05 August 2022

Accepted after revision: 27 September 2022

Accepted Manuscript online:
27 September 2022

Article published online:
28 November 2022

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