Hydroxyquinones: Synthesis and Reactivity

Abstract

Quinones having hydroxy groups directly attached to the quinone ring constitute a very interesting class of quinoid compounds. A great number of hydroxyquinones are found in nature and the majority of them exhibit unique biological activity. Their syntheses and their main reactivity patterns are reviewed in this paper.

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

“…For instance, in hydroxysubstituted quinones, polarization can lead even to zwitterionic structures, i.e. to synthetically useful ylide formation [36]. Reaction conditions such as solvent changes, temperature etc., were examined in a study of nucleophilic substitutions of methoxy-alkyl-p-benzoquinones related to a regioselective quinone-enamine coupling process for the formation of the nat-mitomycin backbone: a solvent induced reversal of regioselectivity was established by changing polar protic to polar aprotic solvents [37].…”

Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione

“…It is possible that 11 is converted to dihydroxy bis-quinone isomers 13, as in a typical reaction for the preparation of hydroxy quinones from 1,2,4-triacetoxybenzenes. 12 Bis-quinone 13 affords 14 through a retro Diels-Alder reaction. This tendency of triptycene quinones to undergo retro Diels-Alder reactions under basic conditions has also been observed with other triptycene quinonic derivatives.…”

“…In relation to our interest in hydroxyquinones 12 we recently reported 13 the synthesis of triptycene hydroxyquinone 3 and its conversion through phenyliodonium chemistry to triptycene cyclopentenedione, 5. The latter reacts as a dienophile and dipolarophile affording polycyclic adducts 6 bearing the triptycene moiety (Scheme 1).…”

[Hmim][HSO4]: An Efficient and Reusable Catalyst for the Synthesis of Spiro[dibenzo[a,i]-xanthene-14,3'-indoline]-2',8,13-triones and Spironaphthopyran[2,3-d]pyrimidine-5,3'-indolines

“…The chemistry of quinone-annulated heterocycles is dependent largely on the substituent being either on the quinone or on adjacent rings. 15 These activities, combined with diverse chemical behavior make quinones attractive targets in organic synthesis.…”