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Triethylamine-Promoted Oxidative Cyclodimerization of 2H-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study [PDF]

open access: yesMolecules, 2023
An unprecedented oxidative cyclodimerization reaction of 2H-azirine-2-carboxylates to pyrimidine-4,6-dicarboxylates under heating with triethylamine in air is described. In this reaction, one azirine molecule undergoes formal cleavage across the C-C bond
Timofei N. Zakharov   +4 more
doaj   +2 more sources

5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids [PDF]

open access: yesMolecules, 2022
Amides, anhydrides, esters, and thioesters of 2H-azirine-2-carboxylic acids were prepared by a rapid procedure at room temperature involving FeCl2-catalyzed isomerization of 5-chloroisoxazoles to 2H-azirine-2-carbonyl chlorides, followed by reaction with
Anastasiya V. Agafonova   +2 more
doaj   +2 more sources

Azirinyl-Substituted Nitrile Oxides: Generation and Use in the Synthesis of Isoxazole Containing Heterocyclic Hybrids [PDF]

open access: yesMolecules
The procedure for the generation of azirinyl-substituted nitrile oxides by the reaction of 2-(diazoacetyl)-2H-azirines with tert-butyl nitrite while preserving the azirine ring has been developed.
Alexander S. Dudik   +4 more
doaj   +2 more sources

Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives [PDF]

open access: yesBeilstein Journal of Organic Chemistry
Methods for the preparation of 3-aryl-2H-azirine-2,2-dicarboxylic acids and their amides, esters, and azides by FeCl2-catalyzed isomerization of 3-aryl-5-chloroisoxazole-4-carbonyl chlorides into 3-aryl-2H-azirine-2,2-dicarbonyl dichlorides followed by ...
Anastasiya V. Agafonova   +2 more
doaj   +2 more sources

Azirine ligation: fast and selective protein conjugation via photoinduced azirine–alkene cycloaddition [PDF]

open access: yesChemical Communications, 2010
We report a new bioorthogonal ligation reaction between p-nitrodiphenylazirine and dimethyl fumarate. This photoinduced azirine-alkene cycloaddition provides a rapid (~2 min) and highly selective route to protein conjugation at neutral pH and room temperature in biological medium.
Qing Lin
exaly   +3 more sources

Acridine–Isoxazole and Acridine–Azirine Hybrids: Synthesis, Photochemical Transformations in the UV/Visible Radiation Boundary Region, and Anticancer Activity [PDF]

open access: yesMolecules
Easy-to-handle N-hydroxyacridinecarbimidoyl chloride hydrochlorides were synthesized as convenient nitrile oxide precursors in the preparation of 3-(acridin-9/2-yl)isoxazole derivatives via 1,3-dipolar cycloaddition with terminal alkynes, 1,1 ...
Ekaterina E. Galenko   +3 more
doaj   +2 more sources

3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles [PDF]

open access: yesBeilstein Journal of Organic Chemistry
A 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
doaj   +2 more sources

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]

open access: yesMolecules, 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.
Pavel A. Sakharov   +3 more
doaj   +2 more sources

Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates [PDF]

open access: yesTetrahedron, 2003
AbstractFor Abstract see ChemInform Abstract in Full Text.
Teresa M V D Pinho E Melo
exaly   +3 more sources

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination [PDF]

open access: yesBeilstein Journal of Organic Chemistry, 2018
The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO ...
Jiyun Sun   +5 more
doaj   +3 more sources

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