72786-84-6Relevant academic research and scientific papers
Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives
Karad, Somnath Narayan,Chung, Wei-Kang,Liu, Rai-Shung
, p. 13004 - 13007 (2015/08/06)
Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.
Gold-catalyzed formal [4π + 2π]-cycloadditions of propiolate derivatives with unactivated nitriles
Karad, Somnath Narayan,Chung, Wei-Kang,Liu, Rai-Shung
, p. 5964 - 5968 (2015/09/28)
Gold-catalyzed hetero-[4π + 2π]-cycloadditions of tert-butyl propiolates with unactivated nitriles are described; the resulting 6H-1,3-oxazin-6-ones are not easily accessible via conventional methods. This new finding enables a one-pot gold-catalyzed synthesis of highly substituted pyridines through sequential gold-catalyzed reactions of tert-butyl propiolates with nitriles, and then with electron-deficient alkynes in the same solvent. The utility of these [4 + 2]-cycloadditions is further expanded with various aldehydes, ketones and 2-phenyloxetane, yielding satisfactory yields of cycloadducts.
Chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal with aldehydes and ketones
Zhang, Jiantao,Xu, Jiaxi
, p. 1733 - 1739 (2013/10/21)
The chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal (1) with aldehydes and ketones in the presence of Et3N was investigated. The results indicate that 1 reacts with aromatic aldehydes with weak electron-donating substituents and cyclic ketones under formation of 6-phenyl-4H-1,3-dioxin-4-one derivatives. However, it reacts with aromatic aldehydes with electron-withdrawing substituents to yield 1,3-diaryl-3-hydroxypropan-1-ones, accompanied by chalcone derivatives in some cases. It did not react with linear ketones, aliphatic aldehydes, and aromatic aldehydes with strong electron-donating substituents. A mechanism for the formation of 1,3-diaryl-3-hydroxypropan-1-ones and chalcone derivatives is proposed. We also tried to react 1 with other unsaturated compounds, including various olefins and nitriles, and cumulated unsaturated compounds, such as N,N′-dialkylcarbodiimines, phenyl isocyanate, isothiocyanate, and CS2. Only with N,N′-dialkylcarbodiimines, the expected cycloaddition took place. Copyright
CHEMISTRY OF OXALYL DERIVATIVES OF METHYL KETONES. XXIII. REACTION OF 5-ARYL-2,3-DIHYDROFURAN-2,3-DIONES WITH ALDEHYDES AND KETONES
Andreichikov, Yu. S.,Gein, L. F.,Plakhina, G. D.
, p. 1995 - 1998 (2007/10/02)
5-Aryl-2,3-dihydrofuran-2,3-diones react with aldehydes, ketones, and α-ketoesters to form 2,2,5,6-tetrasubstituted 1,3-dioxen-4-ones.The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with α-diketones occurs either at one carbonyl group of the α-ketone to form 2,6-disubstituted 1,3-dioxen-4-ones or at both carbonyl groups to form 2,2',6,6'-tetrasubstituted 4,4'-dioxo-2,2'-bi(1,3-dioxenyls).
