Recent Advances in the Chemistry of 2-Acylaziridines

Abstract

This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

Two-Step Construction of Thiophene–Oxazole Dyads with Fluorescent Properties by the Ring Expansion of Aziridines

“…Our strategy is based on the oxidative aminoaziridination of a double bond in substrates such as 1 to form an acyl substituted aziridine 2 , which can be transformed into oxazole 4 through the thermal generation of azomethine ylide 3 undergoing the subsequent 1,5-electrocyclization (Scheme ). Substrates 1 were prepared in 58–95% yields by the Knoevenagel condensation of readily accessible thiophenecarboxaldehydes and methylene active compounds (see the Supporting Information for details) …”

“…However, subjecting several thiophenes 1 to the typical conditions of the oxidative aminoaziridination, no pure aziridines 2 could be isolated, although we observed full conversion of the starting materials after the aziridination reaction, and one major product was usually detected by the thin layer chromatography of reaction mixtures. While the 1 H NMR spectrum of the reaction mixture obtained from the diacetyl substrate 1b (R 1 = COMe, R 2 = Me) shows signals that can be ascribed to the respective aziridine 2b , we observed a fast decomposition of 2b in the chloroform- d 1 solution at room temperature (see the Supporting Information for details).…”

Recent Advances in Synthetic Strategies for the C4a,C9a-Fused Tetracyclic Hydrocarbazole Core Structure of Minfiensine and Related Akuammiline Alkaloids

“…Aziridine is a synthetically useful aminoethyl group equivalent, which is introduced by means of nucleophilic ring-opening reaction. [32][33][34] In 2015, Zhao and co-workers developed a formal [3+2] cycloaddition of indole with aziridines to construct tetracyclic hydrocarbazole (Scheme 7). 35 The formal 36 In this reaction, indole 45 was activated with triethylborane and potassium tert-butoxide, and the resulting borate 46 underwent nucleophilic addition at C3 with allylaziridine 47, followed by cyclization to furnish tetracyclic hydrocarbazole 48 in 38% yield with 2:1 dr.…”

Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides

“…Aziridines have been recognized as valuable N-heterocyclic substrates, since these allow the preparation of versatile building blocks that are useful [1][2][3][4] for organic and medicinal chemistry applications. The aziridine ring-opening mechanism leads to the formation of unnatural amino acids, such as lanthionines.…”