7654-06-0Relevant articles and documents
AZIRIDINE-AZIRINE TRANSFORMATION BY 1,2-ELIMINATION via AN AZIRIDINYL CARBANION INTERMEDIATE
Atkinson, Robert S.,Kelly, Brian J.
, p. 2703 - 2704 (1989)
Desilylation of aziridine (5) by treatment with cesium fluoride in dry dimethylformamide in the presence of benzaldehyde followed by oxidation with manganese dioxide gives the benzoylaziridine (11) in 80percent yield: in the absence of benzaldehyde, the presumed aziridinyl carbanion intermediate (9) gives the aziridine (7) (58percent).
Copper-Catalyzed Sulfonyl Azide-Alkyne Cycloaddition Reactions: Simultaneous Generation and Trapping of Copper-Triazoles and -Ketenimines for the Synthesis of Triazolopyrimidines
Nallagangula, Madhu,Namitharan, Kayambu
, p. 3536 - 3539 (2017)
First simultaneous generation and utilization of both copper-triazole and -ketenimine intermediates in copper-catalyzed sulfonyl azide-alkyne cycloaddition reactions is achieved for the one-pot synthesis of triazolopyrimidines via a novel copper-catalyzed
Copper-Catalyzed Ring-Expansion Cascade of Azirines with Alkynes: Synthesis of Multisubstituted Pyridines at Room Temperature
Sujatha, Chandragiri,Bhatt, Chandra Shekar,Ravva, Mahesh Kumar,Suresh, Anil K.,Namitharan, Kayambu
, p. 3241 - 3244 (2018)
The first intermolecular ring-expansion cascade of azirines with alkynes for the synthesis of pyridines, enabled by a copper/triethylamine catalytic system via simultaneous generation and utilization of yne-enamine and skipped-yne-imine intermediates, is reported. Experimental as well as computational mechanistic studies revealed that the role of triethylamine is crucial in deciding the reaction pathway toward the pyridine products. This process offers a novel, one-step, direct, and practical strategy for the rapid construction of highly substituted pyridines under exceedingly mild conditions, and an installed alkyne functionality.
Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: Access to polyaryl 2: H -imidazoles
Zhu, Zhongzhi,Lin, Hanze,Liang, Baihui,Huang, Junjie,Liang, Wanyi,Chen, Lu,Huang, Yubing,Chen, Xiuwen,Li, Yibiao
supporting information, p. 5621 - 5624 (2020/06/19)
A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N-H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.
Self-Catalyzed Rapid Synthesis of N-Acylated/ N-Formylated α-Aminoketones and N-Hydroxymethylated Formamides from 3-Aryl-2 H-Azirines and 2-Me/Ph-3-Aryl-2 H-Azirines
De, Aramita,Majee, Adinath,Santra, Sougata,Zyryanov, Grigory V.
supporting information, p. 3926 - 3930 (2020/07/14)
A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.
