Recent advances in 1,4-benzoquinone chemistry

Ignatious Abraham,R.T Pardasani,Pushpa Pardasani,Rahul Joshi

doi:10.1590/s0103-50532011000300002

Abstract

1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

Highlights

Quinones are a large class of compounds endowed with rich and fascinating chemistry.1 1,4-Benzoquinone or p-benzoquinone [1] is the basic structure of quinonoid compounds
The comprehensive literature survey pertaining to multiple aspects of quinone chemistry unveiled the sustaining importance of quinonoid compounds in many fields of science
Synthetic organic chemists encouraged by the potential applications of quinones have devised a plethora of synthetic strategies which led to the explosion of articles reporting newer and interesting benzoquinone derivatives

Summary

Introduction

Quinones are a large class of compounds endowed with rich and fascinating chemistry.1 1,4-Benzoquinone or p-benzoquinone [1] is the basic structure of quinonoid compounds. Kaul and co-workers isolated six novel alkylated benzoquinone irisoquins A-F [24,25,26,27,28,29] and a known cytotoxic quinone, irisoquin [30] from the rhizomes of Iris kumaonensis These classes of compounds have attracted considerable attention because of their antioxidant and cytotoxic properties. The fruits of Myrsine africana afforded two new benzoquinone derivatives, methylvilangin [39] and methylanhydrovilangin [40]; while the fruits of Maesa lanceolata afforded two more novel quinones,60 2,5-dihydroxy-3-(nonadec-14-enyl)-benzoquinone [41] and lanciaquinone [42] Gunnera perpensa is another plant with high medicinal value..

60 Metachromin P

88 OCH2CH3

Synthesis of benzoquinones from dimethoxybenzenes

Enolization

Findings

Conclusion