Epoxydibenzo[b,f][1,5]diazocines: From a Hidden Structural Motif to an Efficient Solvent-Free Synthetic Protocol

Wojciech Depa; Bartosz Bisek; Marcin Górecki; Michał Michalak

doi:10.1055/s-0040-1719908

Synthesis, Table of Contents

Synthesis 2022; 54(13): 2991-3004
DOI: 10.1055/s-0040-1719908

short review

Epoxydibenzo[b,f][1,5]diazocines: From a Hidden Structural Motif to an Efficient Solvent-Free Synthetic Protocol

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Abstract

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Abstract

Epoxydiazocines belong to the rare class of small V-shaped molecules, closely related to Tröger’s base. Due to their intriguing, unique structure, they could serve as molecular building blocks for supramolecular chemistry. An extensive review on their synthesis is contained in this article. Moreover, our recent findings devoted to efficient and easily scalable synthesis of fluorinated epoxy[1,5][b,f]diazocines through solvent-free base-catalyzed condensation of ortho-aminophenones is provided. The unique V-shaped structure was confirmed by X-ray crystal structure analysis. Furthermore, the rigidity of the epoxydiazocine skeleton allowed for racemate separation and the configuration of enantiomers was established by combining quantum chemical calculations and chiroptical methods.

1 Introduction

2 Synthetic Efforts Towards Epoxydibenzo[b,f][1,5]diazocines

3 Synthetic Efforts Towards Fluorinated Epoxydibenzo[b,f][1,5]diazocines

4 Conclusion

Key words

epoxydiazocine - aminophenones - condensation - fluorine-containing compound - heterocycles

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References

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