21304-53-0Relevant academic research and scientific papers
Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs2CO3
Guo, Zhengwei,Li, Man,Mou, Xue-Qing,He, Gang,Xue, Xiao-Song,Chen, Gong
supporting information, p. 1684 - 1687 (2018/03/23)
A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3-, enhancing its SET reducing ability to generate an aryl radical from ArI.
Metal-Free sp3 C-H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid
Hu, Ting,Yan, Hao,Liu, Xingxing,Wu, Chaoyang,Fan, Yuxing,Huang, Jing,Huang, Guosheng
supporting information, p. 2866 - 2869 (2015/12/18)
A nonmetal-catalyzed process for the synthesis of polysubstituted oxazoles from inexpensive and readily available α-amino acids and methyl ketones is established. This reaction is proposed to achieve oxidative cleavage of C(sp3)-H bonds, followed by decarboxylation and annulation. The mild reaction conditions employed in both cases enable the tolerance of a wide range of functional groups as well as high reaction efficiency.
Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
Gao, Qing-He,Fei, Zhuan,Zhu, Yan-Ping,Lian, Mi,Jia, Feng-Cheng,Liu, Mei-Cai,She, Neng-Fang,Wu, An-Xin
, p. 22 - 28 (2013/01/15)
An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.
Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines
Beletskii,Kuznetsov
experimental part, p. 1229 - 1240 (2009/12/09)
Oxidative addition of N-aminophthalimide to benzylideneacetone and chalcones followed by thermolysis of the arising 2-aryl-3-acyl-1- phthalimidoaziridines led to the formation of 2,5-disubstituted oxazoles in an overall yield 30-55%. Electron-donor substi
Combinatorial discovery of novel fluorescent dyes based on Dapoxyl
Zhu, Qing,Yoon, Hai-Shin,Parikh, Puja B.,Chang, Young-Tae,Yao, Shao Q.
, p. 5083 - 5086 (2007/10/03)
We have developed a combinatorial method for the fast and effective synthesis of a library based on a known fluorescent dye, Dapoxyl using parallel solution-phase chemistry. By screening the 140 new compounds using fluorescence-based assays, we identified three new fluorescent dyes with novel properties.
Formation of Acyl-Substituted Nitrile Ylides by Rh2(OAc)4-Catalyzed Decomposition of α-Diazocarbonyl Compounds in Nitriles
Fukushima, Kazuaki,Ibata, Toshikazu
, p. 3469 - 3482 (2007/10/03)
The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives.The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of the same intermediate with DMAD.The regiochemistry of the cycloaddition of the acyl-substituted nitrile ylide with methyl propiolate showed that the contribution of an allenyl-type resonance structure plays an important role in the acyl-substituted nitrile ylide reaction.
Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh2(OAc)4-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
Ibata, Toshikazu,Fukushima, Kazuaki
, p. 2197 - 2200 (2007/10/02)
The rhodium(II) acetate-catalyzed reaction of α-diazocarbonyl compounds with benzonitrile and dimethyl acetylenedicarboxylate gave oxazoles and pyrrole-3,4-dicarboxylates through the 1,5-cyclization and 1,3-dipolar cycloaddition of the acyl substituted nitrile ylide intermediates generated by the reaction of ketocarbenoids with benzonitrile.
Synthesis of 2,5-Disubstituted Oxazoles from Aldehydes and N-(Tosylmethyl)imino Synthons. Application to the Synthesis of Pimprinine Analogues
Houwing, Hendrik A.,Wildeman, Jurjen,van Leusen, Albert M.
, p. 1133 - 1139 (2007/10/02)
A series of N-(tosylmethyl)imino compounds has been applied to a new base induced, one-operational synthesis of 2,5-disubstituted oxazoles from aromatic aldehydes.For substituent A of the imino compounds, which becomes the 2-substituent in the oxazoles, has been chosen methoxy, methyl and phenyl.The new method has been used also to synthesize seven pimprinine analogues, i.e., 5-(3-indolyl)oxazoles.
