Chemistry of Nitroaziridines

Abstract

This review article introduced synthetic procedures for the preparation of structurally diverse nitroaziridines. In addition, this article also summarized reactivity of nitroaziridines caused by the inherent strain and high electrophilicity of the small ring. These properties facilitate their use as a functionalized building blocks in synthetic and medicinal chemistry. INTRODUCTION Aziridines are an important class of nitrogen-containing heterocycles that can be found in a number of biologically active compounds, such as mitomycin, porfiromycin, and azinomycin. 1 Due to the inherent ring strain and high electrophilicity, they undergo ring-opening reactions with various nucleophiles to produce a wide range of nitrogen-containing compounds such as amino acids, amino sugars and alkaloids. 2 In contrast to epoxides, aziridines can be readily metalated and reacted with electrophiles, 3 leading to a broader range of functionalized derivatives, which serve as versatile building blocks in organic synthesis. 1,4 Indeed, a substantial number of functionalized aziridines have been transformed into useful products such as an HIV protease inhibitor, 5 communesin, 6 ceramide, 7 and oseltamivir 8 via rearrangement, cycloaddition, and ring expansion reactions. 4 Among various functional groups, the nitro group is highly attractive in synthetic chemistry owing to the strongly electron-withdrawing ability and its versatility for obtaining diverse functionalized compounds by chemical conversion. 9 Considering the above features, we focused our attention on nitroaziridines, which are important synthetic intermediates. 10 Hence, the chemistry of nitroaziridines is reviewed here. This article is dedicated to Professor Tohru Fukuyama on the occasion of his 70th birthday.