127916-11-4Relevant articles and documents
Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions
Ghorbani, Fatemeh,Kiyani, Hamzeh,Pourmousavi, Seied Ali
, p. 943 - 959 (2019/11/13)
Abstract: It was found that nano-SiO2–H2SO4 was catalyzed by the three-component cyclocondensation of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-ketoesters toward the synthesis of α,β-unsaturated?isoxazol-5(4H)-ones under green conditions. The reaction yielded the corresponding heterocycles at room temperature in relatively shorter reaction times. It merits mentioning that the mild conditions allow the synthesis of several α,β-unsaturated?isoxazol-5(4H)-ones using this method. In this study, some new derivatives of isoxazolones were also synthesized and characterized. It is efficient, clean, simple, safe, and ecologically friendly. This straightforward method is cost-effective and requires no preparation of reactants. The three-component annulation was performed without using energy sources, for example, heat, ultrasound wave, and microwave irradiation. Graphic abstract: [Figure not available: see fulltext.].
Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines
Baek, Yonghyeon,Maeng, Chanyoung,Kim, Hyunseok,Lee, Phil Ho
, p. 2349 - 2360 (2018/02/23)
A regioselective synthetic method for the preparation of indolopyrazines was demonstrated through a sequential Rh-catalyzed formal [3+3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint.
Organocatalyzed nucleophilic addition of pyrazoles to 2: H -azirines: Asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2 H -azirines
An, Dong,Guan, Xukai,Guan, Rui,Jin, Lajiao,Zhang, Guangliang,Zhang, Suoqin
supporting information, p. 11211 - 11214 (2016/09/21)
The first organocatalytic asymmetric nucleophilic addition of arylpyrazoles to 2H-azirines and kinetic resolution of racemic 2H-azirines have been realized. Chiral aziridines were obtained with up to 98% yields and up to 99.9% ee. Meanwhile, simply changing the ratio of reactants, optically active 2H-azirines were recovered in good yields with excellent enantioselectivities.
Rh(ii)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: Switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon
Wang, Yuanhao,Lei, Xiaoqiang,Tang, Yefeng
supporting information, p. 4507 - 4510 (2015/03/18)
The Rh(ii)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions. This journal is
RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles
Zhao, Yun-Zhou,Yang, Hai-Bin,Tang, Xiang-Ying,Shi, Min
supporting information, p. 3562 - 3566 (2015/03/04)
RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).
Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines
Loy, Nicole S. Y.,Singh, Alok,Xu, Xianxiu,Park, Cheol-Min
supporting information, p. 2212 - 2216 (2013/04/10)
Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3- benzenedipropionic acid). The formation of the key intermediate is catal
Hydrogen-bonding and C-H...π interactions in ethyl 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylate monohydrate
Silva, Manuela Ramos,Beja, Ana Matos,Paixo, Jose Antonio,Sobral, Abilio J.F.N.,Lopes, Susana H.,Rocha Gonsalves
, p. o685-o687 (2007/10/03)
The hydrogen-bonding and C-H···π interactions in ethyl 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylate monohydrate were studied. In the above compound three strong hydrogen bonds link substituted pyrrole and water molecules to form infinite chains in
Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins
Gazit, Aviv,App, Harald,McMahon, Gerald,Chen, Jefferey,Levitzki, Alexander,Bohmer, Frank D.
, p. 2170 - 2177 (2007/10/03)
A series of 3-indoleacrylonitrile tyrphostins, 2-chloro-3- phenylquinolines, and 3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF- RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol group in tyrphostins active against EGFR kinase inhibition at different sites. The inhibitors showed selectivity for PDGF and were not active against EGF receptor and HER-2/c-ErbB-2 receptor.
