14367-85-2Relevant academic research and scientific papers
Synthesis of 3-nitroindoles by sequential paired electrolysis
Kilmartin, Paul A.,Lindsay, Ashley C.,Sperry, Jonathan
supporting information, p. 7903 - 7913 (2021/09/28)
3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceedsviaa sequential paired electrolysis process, beginning with anodic oxidation of iodide (I?) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.
Polysubstituted quinazoline derivatives, and preparation method, pharmaceutical composition and application thereof
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Paragraph 0077-0083, (2020/09/20)
The invention relates to polysubstituted quinazoline derivatives, and a preparation method, a pharmaceutical composition and application thereof. The polysubstituted quinazoline derivatives are represented by formula (I), are a PI3K/HDAC dual inhibitor and can be used for preventing and/or treating diseases related to PI3K and/or HDAC activity, such as tumors, autoimmune diseases, kidney diseases,cardiovascular diseases, inflammation, metabolic/endocrine dysfunction or neurological diseases.
Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones
Wang, Zexu,Wu, Xiaofan,Li, Zhining,Huang, Zedu,Chen, Fener
supporting information, p. 3575 - 3580 (2019/04/14)
We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.
Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols
Gharui, Chandan,Behera, Debasmita,Pan, Subhas Chandra
, p. 4502 - 4508 (2018/11/10)
An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).
Organocatalytic Asymmetric Michael/Hemiketalization/Retro-aldol Reaction of α-Nitroketones with Unsaturated Pyrazolones: Synthesis of 3-Acyloxy Pyrazoles
Maity, Rajendra,Gharui, Chandan,Sil, Arun K.,Pan, Subhas Chandra
, p. 662 - 665 (2017/02/10)
An organocatalytic asymmetric cascade Michael/hemiketalization/retro-aldol reaction between unsaturated pyrazolones and α-nitroketones is described. A bifunctional thiourea catalyst was found to be efficient for this reaction. With 10 mol % of catalyst, high yields as well as excellent enantioselectivities are attained for a variety of 3-acyloxy pyrazoles under mild reaction conditions.
Rhodium-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins: A new approach to chiral β-amino nitroalkanes
Zhou, Ming,Dong, Dejun,Zhu, Baolin,Geng, Huiling,Wang, Yan,Zhang, Xumu
, p. 5524 - 5527 (2013/11/19)
An efficient and highly enantioselective catalytic asymmetric hydrogenation of β-acylamino nitroolefins has been realized by using Rh-TangPhos as the catalyst. A series of β-amino nitroalkane products, which are versatile intermediates in organic synthesis, were obtained with high yield and good enantioselectivity.
Highly enantioselective reduction of β-amino nitroolefins with a simple n-sulfinyl urea as bifunctional catalyst
Liu, Xiang-Wei,Yan, Yan,Wang, Yong-Qiang,Wang, Chao,Sun, Jian
, p. 9204 - 9207 (2012/08/27)
Simple but effective: A structurally simple N-sulfinyl urea was found to be a highly efficient bifunctional catalyst, which allows for the development of a novel pathway for the construction of chiral β-amino nitroalkanes through enantioselective reduction of β-amino nitroolefins by trichlorosilane. High yields and excellent enantioselectivities were obtained for a broad range of β-arylamino nitroolefin substrates (see scheme). Copyright
Asymmetric Rh(II)-catalyzed cyclopropanation of alkenes with diacceptor diazo compounds: P -methoxyphenyl ketone as a general stereoselectivity controlling group
Lindsay, Vincent N. G.,Nicolas, Cyril,Charette, Andre B.
supporting information; experimental part, p. 8972 - 8981 (2011/08/04)
Different diacceptor diazo compounds bearing an α-PMP-ketone group were found to be effective carbene precursors for the highly stereoselective Rh2(S-TCPTTL)4-catalyzed cyclopropanation of alkenes (EWG = NO2, CN, CO2Me). The resulting products were readily transformed into a variety of biologically relevant enantiopure molecules, such as cyclopropane α- and β-amino acid derivatives. Different mechanistic studies carried out led to a rationale for the high diastereo- and enantioselectivity obtained, where the PMP-ketone moiety was found to play a critical role in the stereoinduction process. Additionally, the use of catalytic amounts of achiral Lewis bases to influence the enantioinduction of the reactions developed is documented.
Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones
Lee, Jung June,Kim, Jihye,Jun, Young Moo,Lee, Byung Min,Kim, Byeong Hyo
experimental part, p. 8821 - 8831 (2009/12/26)
One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.
Experimental evidence for the all-up reactive conformation of chiral rhodium(II) carboxylate catalysts: Enantioselective synthesis of cis-cyclopropane α-amino acids
Lindsay, Vincent N. G.,Lin, Wei,Charette, Andre B.
supporting information; experimental part, p. 16383 - 16385 (2010/02/16)
(Chemical Equation Presented) Useful empirical insights onto the enantioinduction process of chiral Rh(II)-carboxylate catalysts are described in the first catalytic asymmetric cyclopropanation of alkenes with α-nitro diazoacetophenones. X-ray, solution N
