Functional group made of a carbon-carbon-nitrogen heterocycle
For the parent compound, see Aziridine.
Mitomycin C, an aziridine, is used as a chemotherapeutic agent by virtue of its antitumour activity.[1]
In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−)4C2N−R), a three-membered heterocycle with one amine (>NR) and two methylene bridges (>CR2).[2][3][4] The parent compound is aziridine (or ethylene imine), with molecular formula C2H4NH. Several drugs feature aziridine rings, including mitomycin C, porfiromycin, and azinomycin B (carzinophilin).[5]
^Tomasz, Maria (September 1995). "Mitomycin C: small, fast and deadly (but very selective)". Chemistry and Biology. 2 (9): 575–579. doi:10.1016/1074-5521(95)90120-5. PMID 9383461.
^Gilchrist, T.L. (1987). Heterocyclic chemistry. ISBN 978-0-582-01421-3.
^Epoxides and Aziridines – A Mini Review Albert Padwa and S. Shaun Murphree Arkivoc (JC-1522R) pp. 6–33 Online article
^Sweeney, J. B. (2002). "Aziridines: Epoxides' ugly cousins?". Chem. Soc. Rev. 31 (5): 247–258. doi:10.1039/B006015L. PMID 12357722.
^Ismail, Fyaz M.D.; Levitsky, Dmitri O.; Dembitsky, Valery M. (2009). "Aziridine alkaloids as potential therapeutic agents". European Journal of Medicinal Chemistry. 44 (9): 3373–3387. doi:10.1016/j.ejmech.2009.05.013. PMID 19540628.
practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest...
In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−)4C2N−R), a three-membered heterocycle...
pharmaceuticals. Azomethine ylides can be generated from many sources, including aziridines, imines, and iminiums. They are often generated in situ, and immediately...
3-tetrasubstituted aziridines from α-chloroketimines". Tetrahedron. 46 (8): 2965–2974. doi:10.1016/S0040-4020(01)88388-5. "Asymmetric Synthesis of Aziridines by Reduction...
isoindole: Nitrene cycloaddition. With alkenes, nitrenes react to form aziridines, very often with nitrenoid precursors such as nosyl- or tosyl-substituted...
Chloride Promoted Highly Regioselective Ring Opening of Epoxides and Aziridines Using NaN 3 in Acetonitrile: A Facile Synthesis of 1,2-Azidoalcohols and...
oxazaphosphorines, alkyl alkane, sulphonates, nitrosoureas, tetrazines and aziridines." Malignancy has been a constant global health concern for a number of...
(2013-08-20). "Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines". Journal of the American Chemical Society. 135 (36): 13605–13609. doi:10...
unusual conversion of 1-alkyl-2-(bromomethyl)aziridines into 1-alkyl-2-(N-alkyl-N-ethylaminomethyl)aziridines using methyllithium Matthias D'hooghe and Norbert...
R″ groups are constrained in cyclic structures such as N-substituted aziridines (quaternary ammonium salts are resolvable). In aromatic amines ("anilines")...
Aziridiniums are the ionic form of the class of molecules known as aziridines. Aziridines can be used to insert nitrogen atoms during synthesis, but without...
"forward" (epoxide to aziridine) or "reverse" (aziridine to epoxide) direction depending on the conditions employed. Electron-poor aziridines undergo the reverse...
aqueous sodium bisulfite. A direct approach involves the reaction of aziridine with sulfurous acid. In 1993, about 5000–6000 tonnes of taurine were produced...
of an epoxide. Thus, ethylenimine is the three-membered ring species aziridine C2H4NH. The relationship of imines to amines having double and single...
as in the preparation of methylenecyclopropane below. Cyclopropenes, aziridines and cyclobutanes may be formed in a similar manner. Carbon acids which...
ammonia. Intramolecular reactions of haloamines X-(CH2)n-NH2 give cyclic aziridines, azetidines and pyrrolidines. N-alkylation is a general and useful route...
nucleophilic substitution especially to small strained rings like epoxy and aziridines carbonyl-chemistry-like formation of ureas but not reactions of the aldol...
alkylating agents are the nitrogen mustards, nitrosoureas, tetrazines, aziridines, cisplatins and derivatives, and non-classical alkylating agents. Nitrogen...
original on 2012-08-05. Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH...
aldehyde or by thermal ring opening reaction of certain N-substituted aziridines. The further-unsaturated nitrile ylides are known almost exclusively as...
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