951682-11-4Relevant academic research and scientific papers
Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
Meng, Huanxin,Xu, Zhenhua,Qu, Zhonghua,Huang, Huawen,Deng, Guo-Jun
supporting information, p. 6117 - 6121 (2020/08/12)
A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.
Elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles using trifluoroacetic anhydride as reagent
Luo, Beibei,Weng, Zhiqiang
supporting information, p. 10750 - 10753 (2018/09/29)
An elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles from the reaction of acetophenone oxime acetates with trifluoroacetic anhydride has been developed. This new tandem cyclization proceeds in good to excellent yields via a SET reduction followed by a 5-endo-trig pathway. Some of the title compounds showed fungicidal and insecticidal activities.
Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
Zhu, Zhongzhi,Tang, Xiaodong,Cen, Jinghe,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 3767 - 3770 (2018/04/17)
A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.
Synthesis of enaminones via copper-catalyzed decarboxylative coupling reaction under redox-neutral conditions
Zhu, Zhongzhi,Tang, Xiaodong,Li, Jianxiao,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
supporting information, p. 3228 - 3231 (2017/03/20)
A novel copper-catalyzed C(sp3)-H oxidative functionalization of aromatic oxime acetates with α-oxocarboxylic acids was reported. This process involved N-O/C-C bond cleavages and C-C bond formations to furnish substituted enaminones under redox-neutral conditions. The oxime acetates served as both reactants and internal oxidants. Furthermore, this transformation also features good functional group tolerance and needs no ligands or additional bases.
Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions
Zhu, Zhongzhi,Tang, Xiaodong,Li, Jianxiao,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
supporting information, p. 1370 - 1373 (2017/03/23)
A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N-O/N-N bond cleavages and two C-N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands. Furthermore, this is a green reaction involving oxime acetate as internal oxidant, acetic acid, and nitrogen as byproducts.
An efficient synthesis of polysubstituted pyrroles via copper-catalyzed coupling of oxime acetates with dialkyl acetylenedicarboxylates under aerobic conditions
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 9597 - 9599 (2013/10/08)
A Cu-catalyzed [3+2]-type condensation reaction of oxime acetates and dialkyl acetylenedicarboxylates that provides highly substituted pyrroles under aerobic conditions is described. The newly formed pyrroles are easily employed for further transformations to prepare pyrrolo[2,1-a]isoquinoline skeletons. The Royal Society of Chemistry 2013.
O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization
Neufeldt, Sharon R.,Sanford, Melanie S.
supporting information; experimental part, p. 532 - 535 (2010/05/02)
[Chemical equation presented] O-Acetyl oxlmes serve as effective directing groups for Pd-catalyzed sp2 and sp3 C-H functionalization reactions. The C-H functionalization products can be subsequently transformed Into ortho- or β-functionalized ketones, alcohols, amines, and heterocycles.
