1777-61-3Relevant academic research and scientific papers
Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
Abdelli, Abderrahmen,Efrit, Mohamed Lotfi,El-Marrouki, Dalel,Gros, Philippe C.,M’Rabet, Hédi,Touchet, Sabrina
supporting information, p. 1722 - 1731 (2021/06/25)
A convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.
Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines
Ding, Xiaojuan,Duan, Jindian,Fang, Zheng,Guo, Kai,Li, Zhenjiang,Mao, Yiyang,Rong, Binsen,Xu, Gaochen,Zhang, Lei,Zhu, Ning
supporting information, p. 2532 - 2542 (2020/03/13)
The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.
Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium
Chen, Zhili,Hu, Fangli,Huang, Shengli,Zhao, Zhengxing,Mao, Hui,Qin, Wenling
, p. 8100 - 8111 (2019/06/17)
Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions
Xie, Peizhong,Fu, Weishan,Cai, Xinying,Sun, Zuolian,Wu, Ying,Li, Shuangshuang,Gao, Cuiqing,Yang, Xiaobo,Loh, Teck-Peng
, p. 7055 - 7059 (2019/09/12)
A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.
Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
Liu, Xiao-Dong,Ma, Hai-Yan,Xing, Chun-Hui,Lu, Long
, p. 1780 - 1783 (2017/07/27)
NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.
Iodine-mediated intramolecular amination of ketones: The synthesis of 2-acylindoles and 2-acylindolines by tuning N-protecting groups
Gao, Wen-Chao,Jiang, Shan,Wang, Ruo-Lin,Zhang, Chi
, p. 4890 - 4892 (2013/07/05)
A general method for constructing both 2-acylindoles and 2-acylindolines via I2-mediated intramolecular C-N bond formation is presented, and the selective formation of either 2-acylindoles or 2-acylindolines just depends on the nitrogen protecting groups used in the same substrate skeletons. The Royal Society of Chemistry.
Edge-Shared [M2Cl10]2- complexes of reaction between oxophilic group 4 metal and phosphorus ylides1
Sabounchei,Ahmadi,Shahriari,Hoseini-Fashami,Samiee
, p. 1005 - 1013 (2012/10/08)
The reactions between oxophilic group 4 metal chlorides, α-keto ylides in THF, led to the forma-tion of titanium, zirconium and hafnium edge-shared [M2Cl10]2- complexes (1a-3f). We describe that the reaction between MClsu
New access to trisubstitutea 3-pyrrolines under phosphine catalysis
Schuler, Marie,Duvvuru, Deepti,Retailleau, Pascal,Betzer, Jean-Francois,Marinetti, Angela
supporting information; scheme or table, p. 4406 - 4409 (2009/12/26)
Conjugated dienes, properly activated by electron-withdrawing groups on both ends, are shown to be suitable substrates for phosphinepromoted organocatalytic processes. Their reactions with imines, under phosphine catalysis, afford a new and efficient synthetic approach to functionalized 3-pyrrolines.
Synthesis and characterization of transition metal (Hg(II), Ag(I) and Cd(II)) complexes of some new: Phosphorus ylides
Sabounchei, S. Javad,Jodaian, Vida,Nemattalab, Hassan
experimental part, p. 9 - 13 (2010/08/19)
Reaction of two new phosphorus ylides Ph3PCHCOC 10H7 (Y1) and Ph3PCHCOC 4H3S(Y2) with mercury(II) halides and a previously reported ylide (P-tolyl)3PCHCOOCH
Synthesis and NMR study of α-keto stabilized ylides of the type RCOCH=PAr3, (R=MeO-C6H4, Cl-C6H 4, NO2-C6H4, α-thiophenyl and naphthyl; Ar = p-tolyl or phenyl)
Sabounchei, Seyyed Javad,Nemattalab, Hassan,Jodaian, Vida
scheme or table, p. 197 - 200 (2009/04/06)
Synthesis and characterization of five new phosphonium salts and related phosphorus ylides of the type R-COCH=PAr3 are reported. The reaction of bromo 4′-methoxo/chloro/nitro acetophenone, α-thiophenyl and naphthoyl acetophenone with triphenylp
