3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles [PDF]
Beilstein Journal of Organic ChemistryA high-yielding method for the synthesis of 3-arylbenzo[4,5]thieno[3,2-b]pyrroles has been developed via pyrrole ring annulation to the aromatic benzo[b]thiophene system, using 3-arylazirines as a N‒C=C synthon.
Julia I. Pavlenko +5 more
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Substituent Effects Govern the Efficiency of Isoxazole Photoisomerization to Carbonyl‑2H‑Azirines [PDF]
ACS Organic & Inorganic AuThe photoisomerization of isoxazoles is an atom-economical route to carbonyl-2H-azirines, which are valuable in both synthetic and biological applications.
Kyra E. Jackson +3 more
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Synthesis of Δ1‑Pyrrolines via Formal (3 + 2)-Cycloaddition of 2H‑Azirines with Enones Promoted by Visible Light under Continuous Flow [PDF]
ACS OmegaThis work reports the first synthesis of Δ1-pyrrolines promoted by visible light under continuous flow, achieved through the formal (3 + 2)-cycloaddition of 2H-azirines to enones.
Lorena S. R. Martelli +4 more
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Selective Synthesis of 3‑(1H‑Tetrazol-5-yl)-indoles from 2H‑Azirines and Arynes [PDF]
ACS OmegaA new selective synthetic approach to indole derivatives bearing a tetrazole moiety has been developed. Arynes, generated in situ from o-(trimethylsilyl)aryl triflates and KF, reacted smoothly with 2-(2-benzyl-2H-tetrazol-5-yl)-2H-azirines to give 3-(2 ...
Carla Grosso +6 more
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Copper-Catalyzed Highly Enantioselective Addition of a Silicon Nucleophile to 3-Substituted 2H-Azirines Using an Si-B Reagent. [PDF]
Angew Chem Int Ed Engl, 2023 3‐Substituted 2H‐azirines can be considered strained cyclic ketimines, and highly enantioselective addition reactions of silicon nucleophiles to either acyclic or cyclic ketimines have been elusive so far.
Zhao ZY, Cui M, Irran E, Oestreich M.
europepmc +2 more sources
A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach [PDF]
Beilstein Journal of Organic Chemistry, 2021 The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds.
Michael Andresini +2 more
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Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds. [PDF]
Molecules, 2022 A method for the [2+3] pyrroline annulation to the six-membered non-aromatic enols using 3-aryl-2H-azirines as annulation agents is developed in the current study.
Sakharov PA +3 more
europepmc +2 more sources
Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines [PDF]
Nature Communications, 2019 Due to their poor electrophilicity, 2H-azirines do not easily react with nucleophiles. Here, the authors show an acidic activation of 2H-azirines by cyanoacetic acid coupling partners affording chiral aziridines containing vicinal tetrasubstituted and ...
Hai-Jun Zhang, Yan-Cheng Xie, Liang Yin
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Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2<i>H</i>-Azirines by Cascade Energy Transfer. [PDF]
J Am Chem SocThe energy transfer (EnT)-catalyzed ring opening and further decarboxylation of isoxazole-5(4H)-ones enables the in situ generation of strained 2H-azirines. Subsequent selective C(sp2)–C(sp3) bond cleavage of the azirine intermediate allows a formal [3 +
Petti A +7 more
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Reactivity of 2<i>H</i>-Azirines in Copper-Catalyzed Azide-Alkyne Cycloaddition Reactions. [PDF]
Org LettA reaction between azide, alkyne and 2H-azirine resulted in C–C bond formation at position five of 1,2,3-triazole, instead of previously misidentified C–N bond connectivity. The reaction mechanism of this C–C bond formation on the triazole ring was fully
Janecký L +5 more
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