Aziridines: epoxides’ ugly cousins?

Abstract

Aziridines, the nitrogenous analogues of epoxides, have until recently excited far less interest amongst synthetic organic chemists than their oxygenated counterparts, with some justification. A range of reviews concerned with the physical properties, synthesis (asymmetric and otherwise), reactions and utility of aziridines exists; this review briefly summarizes the similarities and differences between oxiranes and their nitrogenated analogues, concentrating on the underlying properties of aziridines and recent developments in their chemistry. In addition to descriptions of the physical nature of aziridines, especially those features which underpin their utility as synthetic intermediates, the sections beneath describe reactions involving alkylative ring-opening and synthesis of aziridines.

Synthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores

“…The aziridine moiety represents one of the most valuable three-membered ring systems in organic chemistry [10,11,12,13,14,15,16,17], and the regiocontrolled ring opening of Csubstituted aziridines constitutes a powerful approach towards the preparation of a large variety of nitrogen-containing target compounds. In contrast to their activated counterparts, non-activated aziridines have been evaluated to a limited extent up to now, both from a synthetic and a pharmacological point of view.…”

Highly chemo- and diastereo-selective synthesis of 2,6-diazabicyclo[3.2.0]heptan-7-ones, pyrrolidines and perhydroazirino[2,3-c]pyrroles

“…[22][23][24][25] However, the reported methods for preparation of aziridinopyrrolidines are cumbersome and have multistep reaction procedures. [17][18][19][20][21] Recent publications from our laboratory have reported the synthesis and subsequent transformations of functionalized lactams for the synthesis of (2-oxo-4-styrylazetidin-3-yl)pyridine, butadienyl-4-iminomethylazetidin-2-ones, butenylidene-butadienyl-[2,2′-biazetidine]-4,4′-diones, 1,4-benzodiazepin-2-ones and dienyl thiazolidin-4-ones, [26][27][28] etc. As a part of our ongoing interest in the synthesis of heterocyclic systems, we have reported earlier the metal free diastereoselective synthesis of diazabicyclo[3.2.0]heptan-7-ones and their transformations to functionalized proline esters.…”

“…17,18 Members of this family exhibit potent activity against a variety of cancer cell lines, and were found to be particularly active against solid tumors. [19][20][21] In addition, aziridinopyrrolidines have shown interesting biological properties which makes them important synthetic targets. [22][23][24][25] However, the reported methods for preparation of aziridinopyrrolidines are cumbersome and have multistep reaction procedures.…”

Aziridination of alkenes promoted by iron or ruthenium complexes

“…The aziridine functionality is often responsible for the activity of biologically active species (such as antitumor compounds, antibiotics and enzyme inhibitors) and aziridine containing molecules [2] are also useful building blocks in the synthesis of fine chemicals and pharmaceuticals [3][4][5][6]. The striking chemical properties of aziridines are due to the energy associated to the strained threemembered ring [7], which renders them very active and versatile starting materials for the synthesis of several useful molecules such as amines, amino acids, β-lactams, polymers and α-amido ketones [8,9].…”