Results 151 to 160 of about 3,434 (226)

Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C-N or C-C Azirine Bond in 2-Pyridylazirines.

Organic Letters, 2023
The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion ...
A. Agafonova, Artem A Golubev, I. Smetanin, A. Khlebnikov, D. Spiridonova, M. Novikov   +5 more
semanticscholar   +1 more source

Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates.

Journal of Organic Chemistry, 2022
A diazo strategy for the intramolecular azirine ring expansion was developed. Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates ...
Timur O Zanakhov, E. Galenko, M. Novikov, A. Khlebnikov   +3 more
semanticscholar   +1 more source

A Photoionization Reflectron Time-of-Flight Mass Spectrometric Study on the Detection of Ethynamine (HCCNH2) and 2H-Azirine (c-H2CCHN).

ChemPhysChem, 2021
Ices of acetylene (C 2 H 2 ) and ammonia (NH 3 ) were irradiated with 5 keV electrons to simulate interstellar ices processed by galactic cosmic rays in order to investigate the formation of C 2 H 3 N isomers.
A. Turner, Sankhabrata Chandra, R. Fortenberry, R. Kaiser   +3 more
semanticscholar   +1 more source

Carbamoyl Anion Addition to Azirines

Organic Letters, 2021
The addition of carbamoyl anions to azirines affords synthetically useful 2-aziridinyl amide building blocks. The reaction scope was explored with respect to both formamide and azirine, and the addition was found to be highly diastereoselective. A one-pot conversion of a ketoxime to an aziridinyl amide was demonstrated.
Michael J. Kerner, Christian A. Kuttruff, Maxim Chevliakov, Frederic G. Buono, Donghong A. Gao, Mariusz Krawiec, Carl A. Busacca, Chris H. Senanayake, Peter Wipf, Jonathan T. Reeves   +9 more
openaire   +2 more sources

Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds.

Journal of Organic Chemistry, 2021
The reaction conditions for the Buchner reaction of 2-(diazoacetyl)-2H-azirines with benzene leading to 2-(cyclohepta-2,4,6-trien-1-yl)-2H-azirines have been found.
E. Galenko, Vladimir A Bodunov, M. Kryukova, M. Novikov, A. Khlebnikov   +4 more
semanticscholar   +1 more source

Nucleophile-Induced Rearrangement of 2H-Azirine-2-carbonyl Azides to 2-(1H-Tetrazol-1-yl)acetic Acid Derivatives.

Organic Letters, 2021
2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid.
Nikita I Efimenko, O. Tomashenko, D. Spiridonova, M. Novikov, A. Khlebnikov   +4 more
semanticscholar   +1 more source

Harnessing In Situ Radical Oxygenation: Copper-Catalyzed Interrupted Azirine-Alkyne Ring-Expansion Reaction for the Synthesis of Pyrrolones.

Organic Letters, 2021
Here we report a novel interrupted azirine-alkyne ring-expansion reaction with molecular oxygen for the direct synthesis of highly functionalized pyrrolones enabled by copper catalysis. Mechanistic investigations indicate that the present three-component
Chandragiri Sujatha, Madhu Nallagangula, K. Namitharan   +2 more
semanticscholar   +1 more source

2H-Azirine-based Reagents for Chemoselective Bioconjugation at Carboxyl Residues inside Live Cells.

Journal of the American Chemical Society, 2020
Protein modification by chemical reagents has played an essential role in the treatment of human diseases. However, the reagents currently used are limited to the covalent modification of cysteine and lysine residues.
Nan Ma, Jun Hu, Zhi-Min Zhang, Wenyan Liu, Minhao Huang, Youlong Fan, Xingfeng Yin, Jigang Wang, Ke Ding, W. Ye, Zhengqiu Li   +10 more
semanticscholar   +1 more source

2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks.

Journal of Organic Chemistry, 2020
2H-Azirine-2-carbonyl azides, new reactive heterocyclic building blocks, were synthesized in high yield by the reaction of sodium azide with 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles.
L. Funt, Yulia V. Krivolapova, O. Khoroshilova, M. Novikov, A. Khlebnikov   +4 more
semanticscholar   +1 more source

Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion.

Organic Letters, 2020
A method for the preparation of 5-aminobutenolides from 2-bromo-2H-azirine-2-carboxylic esters/amides with arylacetic acids has been developed. The reaction regioselectivity can be switched by a change of the basic catalyst, making it possible to prepare
P. Sakharov, N. Rostovskii, A. Khlebnikov, M. Novikov   +3 more
semanticscholar   +1 more source