1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis.

Ruan Carlos B Ribeiro,Fernando De Carvalho Da Silva,Vitor F Ferreira,Amanda De A Borges,Luana Da S M Forezi,Patricia G Ferreira

doi:10.3762/bjoc.18.5

Ruan Carlos B Ribeiro, Fernando De Carvalho Da Silva + Show 4 more

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https://doi.org/10.3762/bjoc.18.5

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Abstract

Several low molecular weight naphthoquinones are very useful in organic synthesis. These compounds have given rise to thousands of other naphthoquinones that have been tested against various microorganisms and pharmacological targets, including being used in the preparation of several drugs that are on the pharmaceutical market. Among these naphthoquinones, the series of compounds prepared from 1,2-naphthoquinone-4-sulfonic acid salts (β-NQS) stands out. In addition to being used in organic synthesis, they are excellent analytical derivatization reagents to spectrophotometrically determine drugs containing primary and secondary amino groups. This review summarizes the literature involving β-NQS.

Highlights

The general class of quinones is very important because their compounds show biological activities against several pathogens related to important diseases and are used for the production of special materials [1,2,3,4]
These compounds are biosynthesized by oxidative processes of catecholamines and other compounds, but they can be ingested as exogenous products of air and water
Among all of the compounds in this class, 1,2- and 1,4-naphthoquinones stand out, as they are present in plants, fungi, lichens, bacteria, algae, viruses, insects, and higher organisms and perform several biochemical functions, such as defense, transference of electrons in various oxidative processes in aerobic metabolism, photosynthesis, oxidative phosphorylation, blood clotting, and other electron transport reactions [7,8]

Summary

Introduction

The general class of quinones is very important because their compounds show biological activities against several pathogens related to important diseases and are used for the production of special materials [1,2,3,4]. After the first discovery that β-NQS reacts quickly with amines to form colored products in good yields, this reagent became quite popular in quantitative analytical determinations of some drugs containing free primary and secondary amino groups [50,51]. Β-NQS reacts with aliphatic and aromatic amines, secondary or primary, by substituting the sulfonic acid group at position C4.

Results

Conclusion