Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Abstract

This review discusses the utility of donor-acceptor cyclopropanes (DACs) for the construction of heterocycles. In addition to (3+2), (3+3), and (4+3) cycloaddition pathways, nucleophilic ring-opening reactions, intramolecular transformations, and cycloisomerizations in the presence of suitable catalysts pave the way for the generation of heterocycles from DACs. The mild reactions conditions employed and the variety of starting materials that can be used as reaction partners make the DAC route for heterocycle synthesis attractive. The literature covered in this review is from the period 2018 to 2023.

1 Introduction

2 Synthesis of Nitrogen Heterocycles

2.1 By Annulations with Anthranils and Azadienes

2.2 By Nucleophilic Attack of Anilines and Hydrazones

2.3 By Reaction with Ureas and Thioureas

2.4 By Annulation Reactions Using an Azomethine Imine

2.5 By Reaction with Other Nitrogen Heterocycles

2.6 By Other Transformations

3 Synthesis of Oxygen Heterocycles

3.1 By Intramolecular Transformations

3.2 By Intermolecular Reactions

4 Synthesis of Sulfur and Selenium Heterocycles

4.1 By Reaction with Thiocarbonyl Substrates

4.2 By Reaction with Thio- and Selenocyanates and Thiosulfonate Salts

5 Synthesis of N–S and N–O Heterocycles

6 Conclusions

Key words

donor-acceptor cyclopropanes - heterocycles - annulation - nucleophile - ring-opening

Publication History

Received: 21 March 2023

Accepted after revision: 19 May 2023

Accepted Manuscript online:
22 May 2023

Article published online:
26 June 2023

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