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<title>Aziridines</title>

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Aziridines

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</style><div role="note" class="hatnote navigation-not-searchable">For the parent compound, see <a href="Aziridine" title="Aziridine">Aziridine</a>.</div>

In <a href="Organic_chemistry" title="Organic chemistry">organic chemistry</a>, aziridines are <a href="Organic_compound" title="Organic compound">organic compounds</a> containing the aziridine <a href="Functional_group" title="Functional group">functional group</a> (<a href="Chemical_structure" title="Chemical structure">chemical structure</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">

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</style>(R−)4C2N−R), a three-membered <a href="Heterocycle" class="mw-redirect" title="Heterocycle">heterocycle</a> with one <a href="Amine" title="Amine">amine</a> (>NR) and two <a href="Methylene_bridge" title="Methylene bridge">methylene bridges</a> (>CR2).<a href="#cite_note-2">[2]</a><a href="#cite_note-3">[3]</a><a href="#cite_note-4">[4]</a> The parent compound is <a href="Aziridine" title="Aziridine">aziridine</a> (or ethylene imine), with <a href="Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> C2H4NH. Several drugs feature aziridine rings, including <a href="RMC-9805" title="RMC-9805">zoldonrasib</a>, <a href="Thiotepa" title="Thiotepa">thiotepa</a>, <a href="Mitomycin_C" title="Mitomycin C">mitomycin C</a>, <a href="Porfiromycin" title="Porfiromycin">porfiromycin</a>, and <a href="Azinomycin_B" title="Azinomycin B">azinomycin B</a> (carzinophilin).<a href="#cite_note-bio-5">[5]</a>

<div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2></div>

The <a href="Bond_angle" class="mw-redirect" title="Bond angle">bond angles</a> in aziridine are approximately 60°, considerably less than the normal <a href="Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> bond angle of 109.5°, which results in <a href="Ring_strain" title="Ring strain">angle strain</a> as in the comparable <a href="Cyclopropane" title="Cyclopropane">cyclopropane</a> and <a href="Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> molecules. A <a href="Banana_bond" class="mw-redirect" title="Banana bond">banana bond</a> model explains bonding in such compounds. Aziridine is less <a href="Base_(chemistry)" title="Base (chemistry)">basic</a> than <a href="Open_chain_compound" class="mw-redirect" title="Open chain compound">acyclic</a> <a href="Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> amines, with a <a href="PKa" class="mw-redirect" title="PKa">pKa</a> of 7.9 for the <a href="Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate acid</a>, due to increased <a href="Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">s character</a> of the <a href="Nitrogen" title="Nitrogen">nitrogen</a> <a href="Free_electron_pair" class="mw-redirect" title="Free electron pair">free electron pair</a>. <a href="Angle_strain" class="mw-redirect" title="Angle strain">Angle strain</a> in aziridine also increases the barrier to <a href="Nitrogen_inversion" class="mw-redirect" title="Nitrogen inversion">nitrogen inversion</a>. This barrier height permits the isolation of separate invertomers, for example the <a href="Cis_isomer" class="mw-redirect" title="Cis isomer">cis</a> and <a href="Trans_isomer" class="mw-redirect" title="Trans isomer">trans</a> invertomers of N-chloro-2-methylaziridine.

<div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2></div>

Several routes have been developed for the <a href="Organic_synthesis" title="Organic synthesis">syntheses</a> of aziridines (aziridination).

<div class="mw-heading mw-heading3"><h3 id="Vicinal_cyclization">Vicinal cyclization</h3></div>

<div class="mw-heading mw-heading4"><h4 id="Haloamines,_aminoalcohols_and_azidoalcohols">Haloamines, aminoalcohols and azidoalcohols</h4></div>

In vicinal haloamines, the <a href="Amine" title="Amine">amine</a> functional group spontaneously displaces the adjacent <a href="Halide" title="Halide">halide</a> to generate an aziridine. The reaction is an <a href="Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> <a href="Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a>, similar to the base-induced cyclization of <a href="Halohydrin" title="Halohydrin">halohydrins</a> to epoxides.

With appropriate activating agents, vicinal cyclization is similarly possible with aminoalcohols, themselves efficiently produced from opening epoxides with <a href="Amine" title="Amine">amines</a>.<a href="#cite_note-:0-6">[6]</a>

The parent aziridine is produced industrially from <a href="Aminoethanol" title="Aminoethanol">aminoethanol</a> via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to effect the dehydration. In the <a href="Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a>, the aminoethanol is converted to the <a href="Sulfate_ester" class="mw-redirect" title="Sulfate ester">sulfate ester</a>, which undergoes base-induced sulfate elimination.<a href="#cite_note-Ullmann-7">[7]</a>

In the laboratory, aminoalcohols can be induced to cyclize with the <a href="Mitsunobu_reaction" title="Mitsunobu reaction">Mitsunobu reaction</a>,<a href="#cite_note-:0-6">[6]</a>

but Mitsunobu conditions more fruitfully apply to 2-azido alcohols. Trialkyl phosphines such as <a href="Trimethylphosphine" title="Trimethylphosphine">trimethylphosphine</a> or <a href="Tributylphosphine" title="Tributylphosphine">tributylphosphine</a> reduce azidoalcohols to an α‑alcohol <a href="Phosphine_imide" title="Phosphine imide">phosphine imide</a>, which then cyclizes to an aziridine.<a href="#cite_note-8">[8]</a><a href="#cite_note-9">[9]</a>

In the <a href="Blum-Ittah_aziridine_synthesis" class="mw-redirect" title="Blum-Ittah aziridine synthesis">Blum-Ittah aziridine synthesis</a>, the initial azidoalcohol forms when <a href="Sodium_azide" title="Sodium azide">sodium azide</a> <a href="Ring-opening_reaction" class="mw-redirect" title="Ring-opening reaction">opens</a> an <a href="Epoxide" title="Epoxide">epoxide</a>:<a href="#cite_note-10">[10]</a>

<div class="mw-heading mw-heading4"><h4 id="Darzens-like_reactions">Darzens-like reactions</h4></div>

The <a href="De_Kimpe_aziridine_synthesis" title="De Kimpe aziridine synthesis">De Kimpe aziridine synthesis</a> allows for the generation of aziridines by reacting an <a href="Imine" title="Imine">α-chloroimine</a> with a nucleophile, such as <a href="Hydride" title="Hydride">hydride</a>, <a href="Cyanide" title="Cyanide">cyanide</a>, or a <a href="Grignard_reagent" title="Grignard reagent">Grignard reagent</a>.<a href="#cite_note-11">[11]</a><a href="#cite_note-12">[12]</a>

The <a href="Hoch-Campbell_ethylenimine_synthesis" title="Hoch-Campbell ethylenimine synthesis">Hoch-Campbell ethylenimine synthesis</a> involves the reaction of certain <a href="Oxime" title="Oxime">oximes</a> with <a href="Grignard_reagent" title="Grignard reagent">Grignard reagents</a>, which affords aziridines:<a href="#cite_note-13">[13]</a>

<div class="mw-heading mw-heading3"><h3 id="Nitrene_addition_and_triazoline_contraction">Nitrene addition and triazoline contraction</h3></div>

<a href="Nitrene" title="Nitrene">Nitrene</a> addition to <a href="Alkene" title="Alkene">alkenes</a> is a well-established method for the synthesis of aziridines, and occurs for a wide variety of nitrenoid precursors.

Nitrenes can be prepared in situ when <a href="Iodosobenzene_diacetate" class="mw-redirect" title="Iodosobenzene diacetate">iodosobenzene diacetate</a> oxidizes various <a href="Amide_(functional_group)" title="Amide (functional group)">amides</a>, or from deprotonation of an aminoester:<a href="#cite_note-14">[14]</a>

<a href="Rhodium(II)_acetate" title="Rhodium(II) acetate">Rhodium(II) carboxylates</a> catalyze nitrene formation from O-(2,4-dinitrophenyl)hydroxylamine (DPH), which then aziridates a mono-, di-, tri- or tetra-substituted alkene (olefin):<a href="#cite_note-15">[15]</a>

<dl><dd>alkene + DPH <math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {->[{} \atop {\ce {Rh2(CO2R)4}}]}}}">

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<annotation encoding="application/x-tex">{\displaystyle {\ce {->[{} \atop {\ce {Rh2(CO2R)4}}]}}}</annotation>

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</math><img src="./8e5a7b65e04a482dce436e92f7a2d3a94359ced6.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.028ex; margin-top: -0.386ex; margin-bottom: -0.477ex; width:10.029ex; height:4.676ex;" alt="{\displaystyle {\ce {->[{} \atop {\ce {Rh2(CO2R)4}}]}}}" loading="lazy"> aziridine</dd></dl>

Alternatively, <a href="Photolysis" class="mw-redirect" title="Photolysis">photolysis</a> or <a href="Thermolysis" class="mw-redirect" title="Thermolysis">thermolysis</a> of <a href="Organic_azide" title="Organic azide">organic azides</a> are good ways to generate nitrenes. The same conditions also contract triazolines, expelling <a href="Nitrogen" title="Nitrogen">nitrogen</a> and producing an aziridine.

<div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Nucleophilic_ring_opening">Nucleophilic ring opening</h3></div>

Aziridines are reactive substrates in ring-opening reactions with many <a href="Nucleophile" title="Nucleophile">nucleophiles</a> due to their <a href="Ring_strain" title="Ring strain">ring strain</a>. Alcoholysis and aminolysis are basically the reverse reactions of the cyclizations. Carbon nucleophiles such as <a href="Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a> and <a href="Organocuprate" class="mw-redirect" title="Organocuprate">organocuprates</a> are also effective.<a href="#cite_note-16">[16]</a><a href="#cite_note-17">[17]</a>

One application of a ring-opening reaction in <a href="Asymmetric_synthesis" class="mw-redirect" title="Asymmetric synthesis">asymmetric synthesis</a> is that of <a href="Trimethylsilylazide" class="mw-redirect" title="Trimethylsilylazide">trimethylsilylazide</a> TMSN 3 with an asymmetric ligand<a href="#cite_note-18">[18]</a> in scheme 2<a href="#cite_note-19">[19]</a> in an <a href="Organic_synthesis" title="Organic synthesis">organic synthesis</a> of <a href="Oseltamivir_total_synthesis" title="Oseltamivir total synthesis">oseltamivir</a>:

<div class="mw-heading mw-heading3"><h3 id="1,3-dipole_formation">1,3-dipole formation</h3></div>

Certain N-substituted azirines with <a href="Electron_withdrawing_group" class="mw-redirect" title="Electron withdrawing group">electron withdrawing groups</a> on both carbons form <a href="Azomethine_ylide" title="Azomethine ylide">azomethine ylides</a> in an <a href="Electrocyclic_reaction" title="Electrocyclic reaction">electrocyclic</a> thermal or photochemical <a href="Ring-opening_reaction" class="mw-redirect" title="Ring-opening reaction">ring-opening reaction</a>.<a href="#cite_note-20">[20]</a><a href="#cite_note-21">[21]</a> These ylides can be trapped with a suitable <a href="Dipolarophile" class="mw-redirect" title="Dipolarophile">dipolarophile</a> in a <a href="1%2C3-dipolar_cycloaddition" class="mw-redirect" title="1,3-dipolar cycloaddition">1,3-dipolar cycloaddition</a>.<a href="#cite_note-22">[22]</a>

When the N-substituent is an <a href="Electron-withdrawing_group" title="Electron-withdrawing group">electron-withdrawing group</a> such as a <a href="Tosyl" class="mw-redirect" title="Tosyl">tosyl</a> group, the <a href="Carbon-nitrogen_bond" class="mw-redirect" title="Carbon-nitrogen bond">carbon-nitrogen bond</a> breaks, forming another <a href="Zwitterion" title="Zwitterion">zwitterion</a> TsN− –CH 2–CH+ 2–R<a href="#cite_note-23">[23]</a>

This reaction type requires a <a href="Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> catalyst such as <a href="Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a>. In this way 2-phenyl-N-tosylaziridine reacts with alkynes, <a href="Nitrile" title="Nitrile">nitriles</a>, <a href="Ketone" title="Ketone">ketones</a> and <a href="Alkene" title="Alkene">alkenes</a>. Certain 1,4-dipoles form from <a href="Azetidine" title="Azetidine">azetidines</a>.

<div class="mw-heading mw-heading3"><h3 id="Other">Other</h3></div>

Lewis acids, such as B(C 6F 5) 3, can induce decomposition of the ring to a <a href="Carbocation" title="Carbocation">carbocation</a> and linear <a href="Azanide" title="Azanide">azanide</a>, which then attack <a href="Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> moieties in <a href="Tandem_reaction" class="mw-redirect" title="Tandem reaction">tandem</a>.<a href="#cite_note-24">[24]</a> Oxidation to the <a href="N-oxide" class="mw-redirect" title="N-oxide">N-oxide</a> instead induces <a href="Nitroso" title="Nitroso">nitroso</a> compound extrusion, leaving an <a href="Olefin" class="mw-redirect" title="Olefin">olefin</a>.<a href="#cite_note-25">[25]</a>

<div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2></div>

As <a href="Electrophile" title="Electrophile">electrophiles</a>, aziridines are subject to attack and ring-opening by endogenous nucleophiles such as nitrogenous bases in DNA base pairs, resulting in potential mutagenicity.<a href="#cite_note-26">[26]</a><a href="#cite_note-27">[27]</a><a href="#cite_note-28">[28]</a>

The <a href="International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) classifies aziridine compounds as possibly <a href="Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> to humans (<a href="List_of_IARC_Group_2B_carcinogens" class="mw-redirect" title="List of IARC Group 2B carcinogens">IARC Group 2B</a>).<a href="#cite_note-29">[29]</a> In making the overall evaluation, the IARC Working Group took into consideration that aziridine is a direct-acting <a href="Alkylating_agent" class="mw-redirect" title="Alkylating agent">alkylating agent</a>, which is <a href="Mutagenic" class="mw-redirect" title="Mutagenic">mutagenic</a> in a wide range of test systems and forms DNA adducts that are promutagenic. The features that are responsible for their mutagenicity are relevant to their beneficial medicinal properties.<a href="#cite_note-bio-5">[5]</a>

<ul><li><a href="Binary_ethylenimine" title="Binary ethylenimine">Binary ethylenimine</a>, a dimeric form of aziridine</li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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</style><cite id="CITEREFTomasz,_Maria1995" class="citation journal cs1">Tomasz, Maria (September 1995). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F1074-5521%2895%2990120-5">"Mitomycin C: small, fast and deadly (but very selective)"</a>. Chemistry and Biology. 2 (9): 575–579. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F1074-5521%2895%2990120-5">10.1016/1074-5521(95)90120-5</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9383461">9383461</a>.</cite>

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<li id="cite_note-2"><a href="#cite_ref-2">^</a> <cite id="CITEREFGilchrist,_T.L.1987" class="citation book cs1">Gilchrist, T.L. (1987). Heterocyclic chemistry. Longman Scientific & Technical. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-582-01421-3</bdi>.</cite>

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<li id="cite_note-3"><a href="#cite_ref-3">^</a> Epoxides and Aziridines – A Mini Review Albert Padwa and S. Shaun Murphree <a href="Arkivoc" title="Arkivoc">Arkivoc</a> (JC-1522R) pp. 6–33 <a rel="nofollow" class="external text" href="http://www.arkat-usa.org/ark/journal/2006/I03_Coxon/1522/JC-1522R.asp">Online article</a>

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<li id="cite_note-4"><a href="#cite_ref-4">^</a> <cite id="CITEREFSweeney2002" class="citation journal cs1">Sweeney, J. B. (2002). "Aziridines: Epoxides' ugly cousins?". Chem. Soc. Rev. 31 (5): 247–258. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FB006015L">10.1039/B006015L</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12357722">12357722</a>.</cite>

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<li id="cite_note-bio-5">^ <a href="#cite_ref-bio_5-0">a</a> <a href="#cite_ref-bio_5-1">b</a> <cite id="CITEREFIsmailLevitskyDembitsky2009" class="citation journal cs1">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. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejmech.2009.05.013">10.1016/j.ejmech.2009.05.013</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19540628">19540628</a>.</cite>

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<li id="cite_note-:0-6">^ <a href="#cite_ref-:0_6-0">a</a> <a href="#cite_ref-:0_6-1">b</a> <cite id="CITEREFB._PulipakaStephen_C._Bergmeier2008" class="citation journal cs1">B. Pulipaka; Stephen C. Bergmeier (2008). "Synthesis of Hexahydro-1 H -benzo[ c ]chromen-1-amines via the Intramolecular Ring-Opening Reof Aziridines by π-Nucleophiles". Synthesis. 2008 (9): 1420–30. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2008-1072561">10.1055/s-2008-1072561</a>.</cite>

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<li id="cite_note-Ullmann-7"><a href="#cite_ref-Ullmann_7-0">^</a> <cite id="CITEREFSteuerleFeuerhake2006" class="citation encyclopaedia cs1">Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". <a href="Ullmann's_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a>. Weinheim: Wiley-VCH. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a03_239.pub2">10.1002/14356007.a03_239.pub2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3527306730</bdi>.</cite>

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