58272-99-4Relevant academic research and scientific papers
Z/E(C=C)-isomerization of coumarin enamines induced by organic solvents
Traven, Valery F.,Ivanov, Ivan V.,Lebedev, Victor S.,Milevskii, Boris G.,Chibisova, Tat'yana A.,Solov'eva, Natalya P.,Polshakov, Vladimir I.,Kazheva, Olga N.,Alexandrov, Grigorii G.,Dyachenko, Oleg A.
, p. 214 - 216 (2009)
Imines of 3-formyl-4-hydroxycoumarin have been found to exist in E- and Z-ketoenamine forms in a crystal state and undergo Z/E-isomerization around the C=C bond in organic solvents (e.g., CHCl3).
Synthesis and structure of 3-{[aryl (hetaryl)amino]methylene}chromane-2,4-diones and their metal complexes
Burlov,Vlasenko,Uraev,Aleksandrov,Korshunova,Shcherbakov,Garnovskii,Koshchienko, Yu. V.
, (2016)
3-{[Aryl(hetaryl)amino]methylene}chromane-2,4-diones (HL) were synthesized and used for chemical and electrochemical synthesis of Cu(II), Ni(II), and Co(II) complexes of the general formula ML2, as well as the ZnLOOCCH3 complex. The structure of the compl
Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry
Cagide,Silva,Reis,Gaspar,Borges,Gomes,Low
supporting information, p. 2832 - 2835 (2015/02/19)
The discovery of potent and selective monoamine oxidase-B inhibitors for the management of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases is still a challenging endeavor. Herein, we report the discovery of two new classes of poten
POCl3-mediated synthesis of 2-N-arylimino-4-chloro-3- dichloromethylcoumarin and its conversion into 6H-[1]benzopyrano[4,3-b]quinolin- 6-one
Maiti, Sourav,Biswas, Pritam,Ghosh, Jaydip,Bandyopadhyay, Chandrakanta
, p. 1617 - 1623 (2014/01/17)
On heating in POCl3, 2-(N-aryl)aminochromone-3-carbaldehyde produced 2-N-arylimino-4-chloro-3-dichloromethylcoumarin, which undergoes selective acid-catalyzed hydrolysis of its imino function to produce 4-chioro-3-dichloromethylcoumarin. The hy
E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents
Traven,Ivanov,Lebedev,Chibisova,Milevskii,Solov'Eva,Polshakov,Alexandrov,Kazheva,Dyachenko
body text, p. 1605 - 1611 (2011/05/04)
According to 1H and 13C NMR data, enamines of 3-formyl-4-hydroxycoumarin exist in the keto enamine tautomeric form and undergo Z/E-isomerization around the C=C bond in CDCl3, DMSO-d6, and CD3OD at room temperature. The activation energies of E/Z-isomerization were measured experimentally and calculated by the B3LYP/6-311++G(d,p) method. An X-ray diffraction study showed that 3-(benzyliminomethyl)chromane-2,4-dione in the crystalline state exists as a mixture of two keto enamine isomers.
Rearrangements of N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1- benzopyran-3-carboxaldehyde - A solvent-dependent process
Ghosh, Tarun,Bandyopadhyay, Chandrakanta
, p. 6169 - 6172 (2007/10/03)
C-(4-Oxo-4H-1-benzopyran-3-yl)-N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1-benzopyran-3-carboxaldehyde, rearrange to 2-alkyl-/aryl-amino-3- formylchromone and/or 3-(alkyl-/aryl-aminomethylene)chroman-2,4-dione depending upon the reaction medium. 3-(Alkylaminomethylene)chroman-2,4-dione has been utilized in the synthesis of 1-benzopyrano[3,4-d]isoxazole-4-one.
Contributions to the Chemistry of Enaminoketones, XV: The Three-Component Synthesis of Hydrazinomethylene-chromandiones and a reductive N-N Bond Cleavage of Phenylhydrazine
Junek, H.,Reidlinger, C.
, p. 579 - 586 (2007/10/02)
The three-component reaction of 4-hydroxycoumarin, ethylorthoformiate, and different substituted hydrazines is described. p-Nitrophenylhydrazine, hydrazides and phenylsemicarbazide lead to the expected hydrazinomethylene-chromandiones 2a-f.Reaction of 4-hydroxycoumarin, ethylorthoformiate, and phenylhydrazine or p-tolyl-hydrazine does not yield 2, but the anilino-methylene-chromandiones 6a-b.This indicates a reductive N-N bond cleavage to aniline and ammonia under mild conditions. - Keywords: Hydrazinomethylene-chromandiones; Reductive N-N bond cleavage; Anilinomethylenechromandiones
