Synthesis of Biologically Active Heterocycles via a Domino Sequence Involving an S_N2/Thorpe–Ziegler Reaction Step

Abstract

This review highlights methods for the synthesis of five- and six-membered heterocycles and their annulated analogues. These methods are based on anionic domino reactions that have a common step: an S_N2/Thorpe–Ziegler reaction. In addition, data on the biological activity of these heterocycles are summarized.

1 Introduction

2 Synthesis of Thiophenes, Pyrroles, Furans and Other Heterocycles

2.1 Synthesis of 3-Aminothiophenes

2.2 Synthesis of 3-Aminopyrroles

2.3 Synthesis of 3-Aminofurans

3 Synthesis of Bicyclic Heterocyclic Systems

3.1 Thiophenes, Pyrroles and Furans Fused with Five-Membered Heterocycles

3.2 Thiophenes, Pyrroles and Furans Fused with Six-Membered Heterocycles

4 Synthesis of Heterocyclic Compounds Using Three-Step Domino Reactions

5 Synthesis of Heterocyclic Compounds Based on a Combination of Two Domino Reactions

6 Miscellaneous

7 Conclusion

Key words

domino reactions - heterocycles - medicinal chemistry - drug discovery - Thorpe–Ziegler reaction

Publication History

Received: 21 March 2021

Accepted after revision: 10 June 2021

Accepted Manuscript online:
10 June 2021

Article published online:
24 November 2021

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