20359-54-0Relevant academic research and scientific papers
A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects
Ghinato, Simone,Territo, Davide,Maranzana, Andrea,Capriati, Vito,Blangetti, Marco,Prandi, Cristina
, p. 2868 - 2874 (2021/01/21)
We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
Nickel-catalyzed intermolecular insertion of aryl iodides to nitriles: A novel method to synthesize arylketones
Hsieh, Jen-Chieh,Chen, Yen-Chung,Cheng, An-Yi,Tseng, Hsiao-Chun
supporting information; experimental part, p. 1282 - 1285 (2012/04/23)
A novel procedure for the NiCl2(DME)/dppp/Zn system catalyzed intermolecular insertion of aryl iodides to nitriles was developed, which afforded variously substituted arylketone derivatives in moderate to good yields with tolerance of a wide variety of functional groups.
PYRIDAZINONE COMPOUNDS AS CALCILYTICS
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Page/Page column 48-49, (2010/11/27)
Various calcilytic compounds and pharmaceutical compositions containing these compounds are disclosed. Calcilytic compounds are compounds capable of inhibiting calcium receptor activity. Methods for preparing calcilytic compounds, oral bioavailability of calcilytic compounds, and their use as calcium receptor antagonists are also disclosed.
Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Zhang, Zhongxing,Song, Huimin
, p. 7619 - 7624 (2007/10/03)
Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding α-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield.The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation.Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), α-hydroxyalkyl (12 and 13), α-aminoalkyl (14) and acyl (15) substituents.
Reaction of Aldehyde O-Alkyl Oxime with Organometallic Compounds
Itsuno, Shinichi,Miyazaki, Koji,Ito, Koichi
, p. 3033 - 3036 (2007/10/02)
Aldehyde O-alkyl oximes were converted into ketones with high yields when they were treated with alkyllithium compounds or Grignard reagents followed by hydrolysis.Amines as reductive alkylation products of aldehyde O-alkyl oximes were also obtained by BH3 reduction before hydrolysis.
An Investigation into the Formation of Benzo- and Naphtho-pyrans by Cyclisation of ortho-Alkenyl(hydroxyalkyl)benzenes using either Cerium(IV) Ammonium Nitrate or Potassium t-Butoxide in Dimethylformamide
Giles, Robin G. F.,Green, Ivan R.,Pestana, J. Alexandre X.
, p. 2389 - 2396 (2007/10/02)
A series of ortho-alkenylbenzyl alcohols carrying methoxy substituents at appropriate positions on the aromatic ring have been synthesised.Each of these compounds has been treated separately with each of the title reagents.
A CONVENIENT METHOD FOR THE DIRECT PREPARATION OF KETONES FROM 2-(6-(2-METHOXYETHYL)PYRIDYL) CARBOXYLATES AND ALKYL IODIDES BY USE OF ZINC DUST AND A CATALYTIC AMOUNT OF NICKEL DICHLORIDE
Onaka, Makoto,Matsuoka, Yoshio,Mukaiyama, Teruaki
, p. 531 - 534 (2007/10/02)
Treatment of 2-(6-(2-methoxyethyl)pyridyl) carboxylates with alkyl iodides in the presence of zinc dust and a catalytic amount of NiCl2 in DMF at 50 deg C affords unsymmetrical ketones in good yields by a one-pot procedure.
