10562-00-2Relevant academic research and scientific papers
PIDA-Mediated Formal Olefinic C=C Bond Cleavage of α-Oxo-Ketene N,N-Acetals toward Substituted Oxazolines
Guo, Tenglong,Huang, Fei,Jiang, Quanbin,Yu, Zhengkun
supporting information, p. 14368 - 14372 (2018/09/14)
The hypervalent iodine reagent PhI(OAc)2 (PIDA) mediated the formal oxidative C=C bond cleavage and subsequent cyclization of internal olefins, that is, α-oxo-ketene N,N-acetals, which afforded substituted oxazolines. Isothiazoline derivatives were obtained from the reactions of α-thioxo-ketene N,N-acetals with PIDA under the same conditions. Hydrolysis of the resultant oxazoline derivatives led to highly functionalized oxazolones. A plausible mechanism was proposed based upon the formation of isothiazoline-type intermediates.
Cu-catalyzed aerobic oxidative cyclizations of 3-N-hydroxyamino-1,2-propadienes with alcohols, thiols, and amines to form α-O-, S-, and N-substituted 4-methylquinoline derivatives
Sharma, Pankaj,Liu, Rai-Shung
supporting information, p. 4590 - 4594 (2015/03/18)
A one-pot, two-step synthesis of α-O-, S-, and Nsubstituted 4-methylquinoline derivatives through Cu-catalyzed aerobic oxidations of N-hydroxyaminoallenes with alcohols, thiols, and amines is described. This reaction sequence involves an initial oxidation of N-hydroxyaminoallenes with NuH (Nu = OH, OR, NHR, and SR) to form 3-substituted 2-en-1-ones, followed by Bronsted acid catalyzed intramolecular cyclizations of the resulting products. Our mechanistic analysis suggests that the reactions proceed through a radical-type mechanism rather than a typical ni-trone-intermediate route. The utility of this new Cu-catalyzed reaction is shown by its applicability to the synthesis of several 2-amino-4-methylquinoline derivatives, which are known to be key precursors to several bioactive molecules.
Addition of acetylacetone and ethyl acetoacetate to carbodiimides promoted by nickel acetylacetonate
Dorokhov,Komkov
, p. 676 - 680 (2007/10/03)
The addition reactions of acetylacetone and ethyl acetoacetate with diphenylcarbodiimide and dicyclohexylcarbodiimide in the presence of nickel acetylacetonate afforded N,N′-substituted α,α-dioxoketene aminals. Adducts of acetylacetone with carbodiimides
