Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Azirines are three-membered heterocyclic unsaturated (i.e. they contain a double bond) compounds containing a nitrogen atom and related to the saturated analogue aziridine.[1] They are highly reactive yet have been reported in a few natural products such as Dysidazirine. There are two isomers of azirine: 1H-Azirines with a carbon-carbon double bond are not stable and rearrange to the tautomeric 2H-azirine, a compound with a carbon-nitrogen double bond. 2H-Azirines can be considered strained imines and are isolable.
^Teresa M. V. D. Pinho e Melo and Antonio M. d’A. Rocha Gonsalves (2004). "Exploiting 2-Halo-2H-Azirine Chemistry". Current Organic Synthesis. 1 (3): 275–292. doi:10.2174/1570179043366729. Archived from the original on 2006-09-28.
are two isomers of azirine: 1H-Azirines with a carbon-carbon double bond are not stable and rearrange to the tautomeric 2H-azirine, a compound with a...
under UV irradiation, rearranging to oxazole through azirine intermediate. Meanwhile, the azirine intermediate can react with nucleophiles, especially...
which displaces the tosylate group in a nucleophilic displacement to an azirine and added water subsequently hydrolyses it to the aminoketone. The Beckmann...
synthesizing the starting material. The mechanism is unknown. However, azirine intermediates have been isolated. The mechanism is postulated to proceed...
in 1988 in the marine sponge Dysidea fragilis. Chemically, it is a 2H-azirine derivative. Dysidazirine synthesis was reported for the first time in 1995...
Mannich reaction using 2H-azirines and β-ketoamides. The racemic 2H-azirines was first applied and one enantiomer of the 2H-azirine would react with chiral...
Azirinomycin is an antibiotic azirine derivative with the molecular formula C4H5NO2 which is produced by the bacterium Streptomyces aureus. Azirinomycin...
lithium aluminium hydride is a convenient method of aziridine synthesis. Azirines can also be synthesized from the addition product by adding base to eliminate...
Albert (1996). "Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-X Mode: Convenient Route to 3-Oxazolines". The Journal of Organic...
methodology for synthesis of small ring heterocycles such as aziridines, azirines, azetines, as well as of larger ring heterocycles including azepines. Recently...
alternative to electrophilic amination through the intermediacy of an azirine. The wide variety of electrophilic aminating reagents precludes generalization...
scheme 2 in an organic synthesis of oseltamivir: Certain N-substituted azirines with electron withdrawing groups on both carbons form azomethine ylides...
participate in a variety of reactions; vinyl azides 19 decompose into 2H-azirines 20. Alkyl azides with low nitrogen-content ((nC + nO) / nN ≥ 3) are relatively...
and IN3 find use in synthesis a convenient way to make azidiridines and azirines. The chlorine, bromine, and iodine azides have been characterized in the...
electrophilic carbenes to nitriles, by the photochemical ring opening of azirines and by dehydrochlorination of imidoyl chlorides. The latter is the most...
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