Recent Developments in the Chemistry of Quinoneimides

Abstract

This account describes the developments in quinoneimide chemistry during the last two decades, emphasizing the addition of weak nucleophilic systems leading to cycloadducts in most cases.

One‐Pot Oxidative Heteroannulations of N‐Sulfonylanilines with Styrenes for the Construction of 5‐Aminocoumaran Derivatives

“…In situ oxidation of N-tosylaniline in the presence of H 2 O gives an intermediate A, which undergoes aromatization to form N-tosyl-p-aminophenol. This is followed by further oxidation to afford an electrophilic intermediate pquinone monosulfonimide C. [8] With the catalysis of the CF 3 COOH generated in the oxidation reactions, 5-aminocoumaran is constructed from the Michael addition of intermediate C with 4-methoxystyrene and a subsequent intramolecular cyclization. [9] Trace amounts of N-tosyl-p-aminophenol were detected during the oxidation reaction.…”

1,2-Benzoquinones in Diels–Alder reactions, dipolar cycloadditions, nucleophilic additions, multicomponent reactions and more

“…Related investigations also revealed that Lewis acid mediated reactions of o-quinoneimines and o-quinonediimines followed significantly different pathways depending upon the nature of the Lewis acid, allylsilane and temperature. 4 A report on a similar annulation reaction of silyl enol ethers and an o-quinone leading to the formation of benzofuran derivatives is also worth mentioning here. 55 The photochemical annulation reaction of 1,2-naphthoquinone 110 with allyltrimethylsilane 111 also furnished a dihydrobenzofuran derivative 112 (Scheme 35).…”

Cu(II)–Glucose: Sustainable Catalyst for the Synthesis of Quinazolinones in a Biomass-Derived Solvent 2-MethylTHF and Application for the Synthesis of Diproqualone

“…Quinazolinones are one of the most prevalent heterocycles that are diversely found in many natural products, drugs, and biologically important molecules. − As shown in Figure , several of these compounds are also known to be cytotoxic, antifungal, hypnotic, antiendotoxic, etc. to inhibit insulin secretion and smooth muscle contractile activity by attacking the KATP channel activity.…”

“…Previously reported syntheses of these derivatives rely on precursors, such as ortho -amino or ortho -nitro benzoic acids. Owing to the importance of quinazolinones, various synthetic efforts have been made to prepare them from a variety of starting materials. − …”