76483-83-5Relevant articles and documents
Elucidating the mechanism of the asymmetric aza-Michael reaction
Phua, Pim Huat,Mathew, Suju P.,White, Andrew J. P.,De Vries, Johannes G.,Blackmond, Donna G.,Hii, King Kuok
, p. 4602 - 4613 (2007)
The mechanism of the palladium-catalysed asymmetric aza-Michael addition of aniline to α,β-unsaturated N-imide was examined from several aspects using a combination of techniques, including X-ray crystallography, mass spectrometry, NMR, UV/Vis spectroscopy, and kinetic studies. The binding of aniline to the dicationic palladium(II) metal centre was found to occur in two consecutive steps: The binding of the first aniline is fast and reversible, whereas the binding of the second aniline is slower and irreversible. This occurs in competition with the binding of the N-imide, which forms a planar six-membered chelate ring with the metal centre; coordinating through the 1,3-dicarbonyl moiety. Isotopic labelling revealed that the addition of N-H occurs in a highly stereoselective manner, allowing the synthesis of optically active β2- and β2.3-amino acid derivatives. The stereochemistry of the addition is postulated to be syn. In situ kinetic studies provided evidence for product inhibition. The binding of the N-imide to the catalyst was found to be the rate-limiting step. Aniline was found to be an inhibitor of the pre-catalyst. The study culminated in the design of a new reaction protocol. By maintaining a low concentration of the aniline substrate during the course of the reaction, significant enhancement of yield and enantioselectivity can be achieved.
Palladium-Catalyzed Solvent-Controlled Selective Synthesis of Acyl Isoureas and Imides from Amides, Isocyanides, Alcohols and Carboxylates
Cao, Ming,Liu, Liqiu,Tang, Shi,Peng, Zhiyuan,Wang, Yingchun
, p. 1887 - 1895 (2019/03/11)
A highly selective synthesis of acyl isoureas and imides from readily accessible amides, isocyanides, alcohols and carboxylates based on reaction solvent selection is described. In the presence of a catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and cupric acetate, treatment of amides and isocyanides in alcohols at 60 °C provided acyl isoureas in high yields. Interestingly, when other solvents such as acetonitrile was used instead of alcohols, imides were exclusively produced in good to excellent yields via direct N-acylation of amides with carboxylates as the acyl sources. This protocol offers an attractive alternative approach toward isoureas and imides. (Figure presented.).
Compound (by machine translation)
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Paragraph 0292; 0298, (2017/08/02)
[Problem] sensitivity, resolution, and excellent resistance to lithographic and etching the resist composition, a compound useful as a resist composition for, and a method for forming a resist pattern using the resist composition. (1) a compound represented by the general formula [a] '. In the formula, R represents a hydrogen atom, an alkyl group of 1 - 5 carbon atoms, or a group having a carbon number of 1 - 5 alkyl halide group. R1 Is a sulfur atom or an oxygen atom. R2 Is a single bond, - Y21 - O-to-Y22 A group represented by -, - [Y21 - C (=O) - O]M' - Y21 A group represented by -, - O-a Y (=O) - C22 A group represented by -, - Y or21 - O-a C (=O) - Y22 Is a group represented by -. Y21 And Y21 Is, independently, substituted monovalent hydrocarbon group may have 2. M'is an integer of 0 - 3. Y is a perfluoro aromatic hydrocarbon group. [1 a][Drawing] no (by machine translation)
Compound (by machine translation)
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Paragraph 0292; 0298; 0303, (2017/07/05)
PROBLEM TO BE SOLVED: sensitivity, resolution, lithography and etching resist composition excellent in resistance characteristics, the compound useful as, the resist pattern forming method. SOLUTION: a compound represented by general eq. (1). During eq. (1), R is a hydrogen atom, alkyl group of carbon number 1-5, or halogenated alkyl group of carbon number 1-5. R 1 oxygen atom or a sulfur atom. R 2 divalent linking group a single bond or 2. Y 1 having the polycyclic aliphatic hydrocarbon group (the aliphatic hydrocarbon group, the carbon atom or a hydrogen atom is substituted group may be substituted). [And 1] Selected drawing: no (by machine translation)
RESIST COMPOSITION, METHOD OF FORMING RESIST PATTERN AND POLYMERIC COMPOUND
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Paragraph 0803-0805, (2014/08/19)
A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the base component (A) containing a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below (R1 represents a sulfur atom or an oxygen atom; R2 represents a single bond or a divalent linking group; and Y represents an aromatic hydrocarbon group or an aliphatic hydrocarbon group having a polycyclic group, provided that the aromatic hydrocarbon group or the aliphatic hydrocarbon may have a carbon atom or a hydrogen atom thereof substituted with a substituent.
Efficient Preparations of Acylamides, Acylcarbamates and Acylureas from Alk-1-en-2-yl Esters
Seiller, Benedicte,Heins, Dorothee,Bruneau, Christian,Dixneuf, Pierre H.
, p. 10901 - 10912 (2007/10/02)
Acylamides, acylcarbamates and acylureas have been synthesized by acylation of amides, carbamates and ureas sodium salts with alk-1-en-2-yl esters prepared with 2 as catalyst.
