Synthetically Important Ring-Opening Acylations of Alkoxybenzenes

Dedicated to Professor Yashwant D. Vankar on the occasion of his 70^th birthday

Abstract

Cyclic ketones, anhydrides, lactams and lactones are a particular class of molecules that are often used in synthesis, wherein their electrophilic properties are leveraged to enable facile Friedel–Crafts ring openings through nucleophilic attack at the carbonyl sp² centre. The use of electron-rich alkoxybenzenes as nucleophiles has also become important since the discovery of the Friedel–Crafts reaction. As a result, various isomeric alkoxybenzenes are used for preparing starting materials in target-oriented syntheses. This review covers the instances of different alkoxybenzenes that are used as nucleophiles in ring-opening acylations with carbonyl-containing cyclic electrophiles, for the construction of important building blocks for multistep transformations. This review summarizes the ring-opening functionalization of three- to seven-membered molecular rings with alkoxybenzenes in a Friedel–Crafts fashion. Sometimes the rings need subtle or considerable activation by the help of Lewis acid(s), followed by nucleophilic attack. This review is aimed to be a summary of the important acylations of electron-rich alkoxybenzenes by nucleophilic ring-opening of cyclic molecules. The works cited employ a wide range of conditions and differently substituted substrates for target-oriented syntheses.

1 Introduction and Scope

2 Arenes for Acylative Ring Opening

2.1 Three-Membered Rings: Ring Opening of Oxirane-2,3-dione

2.2 Four-Membered Rings

2.2.1 Ring Opening of Cyclobutanones

2.2.2 Ring Opening of β-Lactams

2.2.3 Ring Opening of β-Lactone

2.3 Five-Membered Rings

2.3.1 Ring Opening of Phthalimides

2.3.2 Ring Opening of γ-Lactones

2.3.3 Ring Opening of Anhydrides

2.4 Six-Membered Rings

2.5 Seven-Membered Rings

3 Conclusion

Key words

Friedel–Crafts acylation - methoxybenzene - dimethoxybenzene - trimethoxybenzene - Lewis acid - β-lactam - β-lactone

Publication History

Received: 18 June 2020

Accepted after revision: 20 July 2020

Article published online:
08 September 2020

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