167558-53-4Relevant academic research and scientific papers
Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives
Wen, Hao,Cao, Wei,Liu, Yu,Wang, Liang,Chen, Ping,Tang, Yu
, p. 13308 - 13324 (2018)
A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted δ-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).
Catalyst-Free [4+2] Cycloaddition of Ynamides with 2-Halomethyl Phenols to Construct 2-Amino-4 H-Chromenes and α-Halo Enamides Simultaneously
Wen, Hao,Yan, Weibo,Chen, Ping,Li, Yu,Tang, Yu
, p. 12870 - 12881 (2020/11/02)
We report the development of a facile protocol for the [4+2] cycloaddition of ynamides and 2-halomethyl phenols to afford the corresponding 2-amino-4H-chromenes and α-halo enamides under catalyst-free conditions. The reaction proceeds under mild condition
A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems
Cao, Wei,Chen, Ping,Wang, Liang,Wen, Hao,Liu, Yu,Wang, Wanshu,Tang, Yu
supporting information, p. 4507 - 4511 (2018/08/09)
A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured α-halo enamides via photocatalysis or under Sonogashira coupling conditions.
Unexpected formation of (Z)-3-(halomethylene)isoindolinones from gem-dihalovinylbenzonitriles: Efficient synthesis of enyne-containing isoindolinones
Wang, Chengming,Sun, Caiyun,Weng, Fei,Gao, Mingchun,Liu, Bingxin,Xu, Bin
supporting information; experimental part, p. 2984 - 2989 (2011/06/21)
An efficient one-pot procedure for the regioselective synthesis of (Z)-3-(halomethylene)-isoindolin-1-ones was developed from easily accessible 2-(2,2-dihalovinyl)benzonitriles. From this key intermediate, a variety of isoindolinones containing an enyne moiety were synthesized in good to excellent yields via palladium-catalyzed Sonogashira reaction. The generated enyne-containing isoindolinones could be further manipulated by iodide induced cyclization reaction to afford a versatile synthetic intermediate 5H-pyrrolo[2,1-a]isoindolol-5-one in high yield and could be further elaborated.
A tandem elimination-cyclization-suzuki approach: Efficient one-pot synthesis of functionalized (Z)-3-(arylmethylene)isoindolin-1-ones
Sun, Caiyun,Xu, Bin
supporting information; experimental part, p. 7361 - 7364 (2009/05/07)
(Chemical Equation Presented) A novel and efficient one-pot regioselective elimination-cyclization-Suzuki approach was developed to afford (Z)-3-arylmethyleneisoindolin-1-ones in good to excellent yields from easily accessible o-gem-dihalovinylbenzamides and organoboron reagents.
An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives
Huh, Dal Ho,Jeong, Ji Sang,Lee, Hee Bong,Ryu, Hoejin,Kim, Young Gyu
, p. 9925 - 9932 (2007/10/03)
Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions.
The Stille Reaction of 1,1-Dibromo-1-alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes
Shen, Wang,Wang, Le
, p. 8873 - 8879 (2007/10/03)
The Stille reaction of 1,1-dibromo-1-alkenes 1 with aryl- and vinylstannanes produces different products depending on the reaction conditions. When the reaction is run in toluene or 1,4-dioxane with tris(2-furyl)phosphine (TFP) as the ligand, (Z)-bromoalkenes 2 are obtained stereospecifically in good to excellent yields with most substrates. However, 2-aryl-1,1-dibromo-1-alkenes (1e,1g) having an electron-donating methoxy group in the para- or ortho- position give poor yields. This method has been applied to the one-pot syntheses of stereospecifically trisubstituted alkenes 5. When the Stille reaction is conducted in a highly dipolar solvent (DMF), monobromides 2 and/or internal alkynes 4 are the products. The less reactive phenylstannane favors the formation of alkynes 4, regardless of which ligand is used. More reactive organostannanes (vinyl, furyl) require a very electron rich ligand, tris(4-methoxyphenyl)phosphine, for the formation of alkynes 4. This new method for internal alkyne preparation is general, requires very mild reaction conditions, and gives high yields.
Electrophilic Reactions of Carbenoids. Synthesis of Fused Heterocyclic Systems via Intramolecular Nucleophilic Substitution of Carbenoids
Topolski, Marek
, p. 5588 - 5594 (2007/10/03)
Intramolecular nucleophilic substitution of carbenoids with oxygen, nitrogen, and sulfur nucleophiles leading to the synthesis of fused heterocyclic compounds has been studied.For the purpose of this investigation styryl type gem-dihalides 4, 8, 18, 20, 28 containing a nucleophilic substituent in the ortho position of the aromatic ring have been synthesized.Carbenoids have been generated in those systems by the halogen - metal exchange reaction and shown to readily undergo intramolecular nucleophilic substitution by the properly located nucleophilic group (OH, SH, or NH2).As a result a new synthetic route to benzofurans, thianaphthenes, and indoles has been established based on nucleophilic substitution of vinyl halides by an ortho substituent.The dramatic increase of reactivity of vinyl halides upon introduction of lithium has been explained as being due to metal-assisted ionization.
