Chemistry of Ring‐Fused Oxazine‐2,4‐diones

Abstract

Isatoic anhydride has attracted a great deal of attention in the last decades. Substitution of its benzene moiety by many different ring systems has given rise to a large array of analogues. A review on the methods of preparation of all known ring‐fused oxazine‐2,4‐diones is given herein. The different reactivity of these analogues is exhaustively depicted andillustrates the rich versatility of this class of starting material.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery

“…Ring-fused oxazine-2,4-diones are of interest for synthetic purposes, but recently, so-called isatoic anhydrides have also been used as tools for bioconjugation. Their water-solubility and the intrinsic chromophore absorbing at wavelengths outside the biological window, thus facilitating their quantification, render them particularly suitable for this type of chemistry .…”

Copper‐Catalyzed Electrophilic Arylation of Isatoic Anhydride with Diaryliodonium Salts for Synthesis of N‐Phenylated Isatoic Anhydrides

“…For now, isatoic anhydride derivatives were mainly obtained by using the cyclization of anhydride, the oxidation of isatin and the rearrangement of anhydride derivatives [3d,8] . Although these approaches bring great convenience to access isatoic anhydride derivatives, the established protocols are mainly confined harsh reaction conditions and are seriously harmful to the environment.…”

Study of Local Reactivity of Isatoic Anhydride Applying Quantum Molecular Similarity

“…Structurally related to anthranilic acid, ISA has been traditionally used as an important scaffold to produce agrochemicals and cosmetics; [1] therefore, considerable efforts have been made to develop safer strategies for their synthesis, since it is known that their derivatives are commonly obtained from cyclization of anthranilic acid by highly toxic chloroformate of triphosgene. [2] Thus, some protocols with palladium catalysed process are available for the synthesis of this important intermediary. [3] Recently, ISA has gained importance as synthetic precursor of known pharmacological agents; its reactivity, characterized by decar-bonylative and ring opening reactions, has been successfully applied in the synthesis of quinazolin-4(3H)-ones, [4] quinazoline benzamides, [5] anilines, [6] and quinolones, [7] in a wide collection of new and outstanding synthetic methodologies.…”