Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Abstract

Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.

1 Introduction

2 Biological Relevance of the cis-1,3-Diamine Motif

3 Classical Synthetic Strategies towards cis-1,3-Diamines

4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines

4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols

4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes

4.3 Synthesis of cis-1,3-Diaminocyclohexitols

4.4 Formation of Cyclic cis-3,5-Diaminopiperidines

5 Applications of Cyclic cis-1,3-Diamines

5.1 Small-Molecular RNA Binders

5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes

6 Concluding Remarks

Key words

cyclic cis-1,3-diamines - bicyclic hydrazines - fragments RNA ligands and probes - N–N bond cleavage - hydroxylation - fluorination - reductive amination

Publication History

Received: 28 August 2020

Accepted after revision: 11 September 2020

Article published online:
19 October 2020

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