86100-38-1Relevant academic research and scientific papers
Palladium-catalyzed c-S activation/aryne insertion/coupling sequence: Synthesis of functionalized 2-quinolinones
Dong, Ying,Liu, Bangyu,Chen, Peng,Liu, Qun,Wang, Mang
supporting information, p. 3442 - 3446 (2014/04/03)
The insertion of an aryne into a C-S bond can suppress the addition of an S nucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc)2, a wide range of α-carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2-quinolinones in high yields under neutral reaction conditions by a C-S activation/aryne insertion/intramolecular coupling sequence. The attractive feature of the new strategy also lies in the versatile transformations of the alkythio-substituted quinolinone products. Within range: Under palladium catalysis a wide range of α-carbamoyl ketene dithioacetals readily react with arynes to selectively afford 2-quinolinones in high yields under neutral reaction conditions by the title sequence (see scheme). An attractive feature of the new strategy also lies in the versatile transformations of the alkylthio-substituted quinolinones.
Amination of phenylketenes. Substituent effect on amine-catalyzed tautomerization of amide enol
Badal, Md. Mizanur Rahman,Zhang, Min,Kobayashi, Shinjiro,Mishima, Masaaki
, p. 1071 - 1076 (2014/01/06)
The transient intermediates with infrared bands at 1676-1680 cm -1 observed for reaction of substituted phenylketenes with diethylamine in acetonitrile were suggested to be the amide enols rather than the zwitterions on the basis of the theoretical calculations. A single broad band at 1674 cm-1 observed for reaction with the primary amines was attributed to overlap of two bands of the intermediate (amide enol) and the final product (amide). The substituent effect for the second-order rate constants of diethylamine-catalyzed tautomerization of the amide enol intermediates to give the amides was analyzed successfully by the Yukawa-Tsuno equation, giving a ρ value of 0.63 and an r- value of 1.31. The r- value larger than unity for pKa of phenols indicates that the negative charge formed at an oxygen atom of the amide enol at the transition state is significantly delocalized into the aromatic π-system through the ethenyl group. This r- value was considered to reflect an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ value attributes to the cyclic transition structure where the negative charge disperses in a six-member ring. Copyright 2013 John Wiley & Sons, Ltd. The substituent effect for the reaction of the amide enol intermediate generated from phenylketene with diethylamine has been analyzed. The large r- of 1.31 was attributed to an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ of 0.63 suggested the cyclic transition structure. Copyright
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.
Synthesis of fluorinated enynes via 1-bromo 1-fluoro alkenes
Eddarir, Said,Francesch, Charlette,Mestdagh, Helene,Rolando, Christian
, p. 4449 - 4452 (2007/10/02)
A stereospecific synthesis of fluorinated enynes was performed through palladium catalysed condensation of 1-bromo 1-fluoro 2-arylethylenes, synthetised from 1-carboxyl 1-fluoro 2-arylethylene with monosubstitued alkynes.
Anticonvulsant activity of some 4-aminophenylacetamides
Clark,Davenport
, p. 18 - 20 (2007/10/02)
A series of 4-aminophenylacetamides was prepared and evaluated for anticonsulvant activity. These compounds were prepared during studies designed to determine the relationship between benzamide-like compounds and anticonsulvant effects. Unlike benzamides, these phenylacetamides have a methylene group between the aromatic ring and the amide carbonyl. Consequently, formal conjugation is lost, and the number of conformational degrees of freedom has increased. The compounds were tested in mice against seizures induced by electroshock and pentylenetetrazol, and in the rotorod assay for neurologic deficit. The more active and selective anticonsulvants prepared in this study were those having an additional aromatic ring as part of the substituent on the amide nitrogen. Compound 16, the 4-aminophenylacetamide derived from 2,6-dimethylaniline, was the most potent compound observed (ED50 = 50.50 mg/kg against electroshock-induced convulsions and ED50 = 93.20 mg/kg against pentylenetetrazol-induced convulsions).
