10403-54-0Relevant articles and documents
KI/TBHP-mediated oxidative cross-coupling of enamines and carboxylic acids under metal-free conditions: A facile access to functionalized 2H-azirines
Duan, Xiyan,Kong, Xianglei,Zhao, Xiaoyong,Yang, Kun,Zhou, Huiyun,Zhou, DongJu,Zhang, Yanping,Liu, Jianwei,Ma, Junying,Liu, Ning,Wang, Zhicheng
, p. 1446 - 1450 (2016)
KI/TBHP-mediated oxidative cross coupling of enamines with carboxylic acids has been realized for the synthesis of functionalized 2H-azirines through the azirination of enamine intermediates. The metal-free strategy has several notable features, including the formation of C-O and C-N bonds in a one-pot procedure, broad functional group tolerance, good reaction yields, short reaction time, and high atom economy. It is the first example for direct formation of functionalized 2H-azirines via KI/TBHP-mediated intermolecular cross-coupling of enamines and carboxylic acids.
Vinylnitrene formation from 3,5-diphenyl-isoxazole and 3-benzoyl-2-phenylazirine
Gamage, Disnani W.,Li, Qian,Ranaweera, R. A. A. Upul,Sarkar, Sujan K.,Weragoda, Geethika K.,Carr, Patrick L.,Gudmundsdottir, Anna D.
, p. 11349 - 11356 (2013)
Photolysis of 1 in argon-saturated acetonitrile yields 2, whereas in oxygen-saturated acetonitrile small amounts of benzoic acid and benzamide are formed in addition to 2. Similarly, photolysis of 2 in argon-saturated acetonitrile results in 1 and a trace amount of 3, whereas in oxygen-saturated acetonitrile the major product is 1 in addition to the formation of small amounts of benzoic acid and benzamide. Laser flash photolysis of 1 results in an absorption due to triplet vinylnitrene 4 (broad absorption with λmax at 360 nm, τ = 1.8 μs, acetonitrile) that is formed with a rate constant of 1.2 × 107 s-1 and decays with a rate constant of 5.6 × 105 s-1. Laser flash photolysis of 2 in argon-saturated acetonitrile likewise results in the formation of triplet vinylnitrene 4 but also ylide 5 (λmax at 440 nm, τ = 13 μs). The rate constant for forming 4 in argon-saturated acetonitrile is 1.6 × 107 s-1. In oxygen-saturated acetonitrile, vinylnitrene 4 reacts to form the peroxide radical 6 (λmax 360 nm, ～0.7 μs, acetonitrile) at a rate of 2 × 109 M-1s-1. Density functional theory calculations were performed to aid in the characterization of vinylnitrene 4 and peroxide 6 and to support the proposed mechanism for the formation of these intermediates.
A photochemical one-pot three-component synthesis of tetrasubstituted imidazoles
Pusch, Stefan,Opatz, Till
, p. 5430 - 5433 (2015/01/09)
Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, α-aminonitriles, and isoxazoles. Condensation of the first two components produces α-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C2-C3 bond of the acylazirine. The reaction mechanism was studied by DFT calculations. (Chemical Equation Presented)
