65846-46-0Relevant academic research and scientific papers
Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides
Samanta, Supravat,Donthiri, Ramachandra Reddy,Dinda, Milan,Adimurthy, Subbarayappa
, p. 66718 - 66722 (2015/08/24)
Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.
Copper-mediated formally dehydrative biaryl coupling of azine N -oxides and oxazoles
Odani, Riko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
, p. 2384 - 2391 (2015/04/14)
A copper-mediated formally dehydrative biaryl coupling of azine N-oxides and oxazoles has been developed. The C-C bond-forming process proceeds, accompanied by the removal of the oxygen atom from the azine core, to directly afford the azine-oxazole biaryl linkage. Moreover, this system requires no noble transition metals such as palladium and rhodium, which are common promotors in the related dehydrogenative couplings with the azine N-oxide. Thus, the present protocol can provide a unique and less expensive approach to the azine-containing biheteroaryls of substantial interest in pharmaceutical and medicinal chemistry.
Direct C-H bond arylation of (benzo)oxazoles with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex
Shen, Xiao-Bao,Zhang, Yun,Chen, Wen-Xin,Xiao, Zheng-Kang,Hu, Ting-Ting,Shao, Li-Xiong
supporting information, p. 1984 - 1987 (2014/05/06)
The direct C-H bond arylation of (benzo)oxazoles with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various aryl chlorides were successfully applied as the arylating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzo)oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.
Photoinduced ring transformation of pyrido-[1,2-b]pyridazinium-4-olate
Batori, Sandor,Doepp, Dietrich,Messmer, Andras
, p. 4699 - 4708 (2007/10/02)
The photolytic behavior of the zwitterionic pyrido[1,2-b]pyridazinium-4- olate (1) was studied. A marked difference was observed depending on the wavelength used: irradiation with a light of λ>280 nm resulted in 3-phenyl- 5-(2-pyridyl)isoxazole (2) and 2-phenyl-3-(2-pyridylcarbonyl)azirine (3) as main products, while the use of light of λ280 afforded 2-phenyl-5-(2- pyridyl)-oxazole (5) and 1-amino-1-phenyl-3-(2-pyridyl)prop-1-en-3-one (6) as main products. A mechanistic suggestion is provided.
A New Versatile Synthesis of Oxazoles by Intramolecular Aza-Wittig Reaction
Takeuchi, Hisato,Yanagida, Shun-ichi,Ozaki, Tooru,Hagiwara, Satoshi,Eguchi, Shoji
, p. 431 - 434 (2007/10/02)
A new synthesis of oxazoles by an intramolecular aza-Wittig reaction is described.Readily available α-azido ketones 2 were converted to (Z)-β-(acyloxy)vinyl azides 3 by selective enol acylation.These vinyl azides 3 reacted with triethyl phosphite to afford the corresponding oxazole derivatives 5 via the Staudinger reaction, followed by an intramolecular aza-Wittig reaction.In particular, this oxazole synthesis was useful for oxazoles having acid-labile substituents.
