53012-84-3Relevant academic research and scientific papers
LPAR1 Inhibitor. Medical application and preparation method thereof
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Paragraph 0072-0074; 0081-0082, (2021/10/05)
LPAR1 Inhibitor, medical application and preparation method thereof, and the structural general formula I of the inhibitor is as follows. In-flight RX Alkyl groups selected from H, C1 - C6, COOCH3 , CF3 , NO2 ,
Synthesis of 3-Benzylphthalide Derivatives by Using a TDAE Strategy
Ibrahimi, Maroua,Khoumeri, Omar,Abderrahim, Raoudha,Terme, Thierry,Vanelle, Patrice
, p. 283 - 286 (2020/11/23)
A one-pot synthesis of new 3-benzylphthalide derivatives was developed by using a strategy based on tetrakis(dimethylamino)ethylene (TDAE). The reactions in the presence of TDAE of substituted benzyl chlorides with methyl 2-formylbenzoate or of substitute
Indium-Catalyzed C?F Bond Transformation through Oxymetalation/β-Fluorine Elimination to Access Fluorinated Isocoumarins
Yata, Tetsuji,Nishimoto, Yoshihiro,Chiba, Kouji,Yasuda, Makoto
, p. 8288 - 8294 (2021/05/21)
Fluorinated heterocycles have attracted much attention in the pharmaceutical and agrochemical industries. Many strategies have already been developed to achieve the synthesis of fluorinated heterocycles. Formidable challenges remain, however, in the synthesis of fluorinated isocoumarin derivatives that are among the most alluring structural motifs. Herein, the indium-catalyzed C?F bond transformation of 2-(2,2-difluorovinyl) benzoates is reported, which are readily accessible compounds, to give a diverse array of fluorinated isocoumarins. The present reaction proceeds smoothly using inexpensive reagents: a catalytic amount of indium salt in the presence of zinc salt. A theoretical calculation of potential energy profiles showed that the reaction consists of oxymetalation with the elimination of alkyl halide and the β-fluorine elimination.
Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade
Meng, Jiao-Long,Jiao, Tang-Qian,Chen, Ya-Heng,Fu, Rui,Zhang, Shu-Sheng,Zhao, Qian,Feng, Chen-Guo,Lin, Guo-Qiang
, p. 1564 - 1567 (2018/03/23)
A Zn-mediated propargylation/lactamization cascade reaction with chiral 2-formylbenzoate derived N-tert-butanesulfinyl imines was realized, which provided a practical and efficient method for the synthesis of chiral isoindolinones. High diastereoselectivities (up to 97:3 dr) and good reaction yields were observed for most examined cases.
Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane
Betterley, Nolan M.,Kongsriprapan, Sopanat,Chaturonrutsamee, Suppisak,Deelertpaiboon, Pramchai,Surawatanawong, Panida,Pohmakotr, Manat,Soorukram, Darunee,Reutrakul, Vichai,Kuhakarn, Chutima
, p. 2033 - 2040 (2018/03/21)
Difluoro(phenylsulfanyl)methane (PhSCF 2 H) was found to undergo a reaction with aromatic compounds mediated by SnCl 4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S, S ′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.
A general catalytic route to isoindolinones and tetrahydroisoquinolines: Application in the synthesis of (±)-crispine A
Dhanasekaran, Sivasankaran,Bisai, Vishnumaya,Unhale, Rajshekhar A.,Suneja, Arun,Singh, Vinod K.
supporting information, p. 6068 - 6071 (2015/01/09)
An unprecedented highly efficient Lewis acid catalyzed one-pot cascade has been demonstrated as a general catalytic system for the synthesis of diversely substituted isoindolinones and tetrahydroisoquinolines. The cascade effects one C-C and two C-N bond-
Asymmetric alkynylation/lactamization cascade: An expeditious entry to enantiomerically enriched isoindolinones
Bisai, Vishnumaya,Suneja, Arun,Singh, Vinod K.
supporting information, p. 10737 - 10741 (2015/05/13)
An unprecedented CuI-pybox-diPh-catalyzed highly enantioselective (up to >99% ee) alkynylation/lactamization cascade has been developed as a general catalytic system for the synthesis of diversely substituted isoindolinones of immense biologica
Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization
He, Yuwei,Cheng, Chuyu,Chen, Bin,Duan, Kun,Zhuang, Yue,Yuan, Bo,Zhang, Meisan,Zhou, Yougui,Zhou, Zihong,Su, Yu-Jun,Cao, Rihui,Qiu, Liqin
, p. 6366 - 6369 (2015/01/16)
Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.
Mild and efficient syntheses of diverse isoindolinones from ortho-phthaldehydic acid methylthiomethyl ester
Ghosh, Usha,Bhattacharyya, Rituparna,Keche, Ashish
experimental part, p. 2148 - 2155 (2010/04/29)
A mild and efficient method for the synthesis of diverse isoindolinones from o-phthaldehydic acid methylthiomethyl ester and aliphatic/aromatic amines has been developed. A number of nucleophiles including a hydride ion were successfully added to the intermediate Schiff's base providing isoindolinones, with or without substitution at 3-position. Conditions have also been developed for amines with an integrated nucleophilic group to react in a diverse fashion either to give isoindolinones or tricyclic γ-lactams as single diastereoisomers in very good yield.
Isolation and synthesis of methyl bovinate, an unusual pulvinic acid derivative from Suillus bovinus (Basidiomycetes)
Besl, Helmut,Bresinsky, Andreas,Kilpert, Claus,Marschner, Wolfgang,Schmidt, Helga M.,Steglich, Wolfgang
experimental part, p. 887 - 893 (2009/03/11)
Cultures and fruit bodies of Suillus bovinus produce the pulvinic acid derivative methyl bovinate (4), which contains an extra carbonyl group that bridges ring A of methyl variegatate with the hydroxy group at the central butenolide ring. This unprecedented structure was deduced from the spectroscopic data and confirmed by total synthesis via a grevillin intermediate. In this synthesis, the menthyl group was used for carboxyl protection.
