490-63-1Relevant academic research and scientific papers
Indium-Catalyzed C?F Bond Transformation through Oxymetalation/β-Fluorine Elimination to Access Fluorinated Isocoumarins
Yata, Tetsuji,Nishimoto, Yoshihiro,Chiba, Kouji,Yasuda, Makoto
supporting information, 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 3-Benzylphthalide Derivatives by Using a TDAE Strategy
Ibrahimi, Maroua,Khoumeri, Omar,Abderrahim, Raoudha,Terme, Thierry,Vanelle, Patrice
supporting information, 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
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
supporting information, 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.
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
supporting information, 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.
PHOSPHODIESTERASE 10 INHIBITORS
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Page/Page column 62, (2008/06/13)
The present invention if directed to certain cinnoline compounds that are PDE10 inhibitors, pharmaceutical compositions containing such compounds and processes for preparing such compounds. The invention is also directed to methods of treating diseases mediated by PDE10 enzyme, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes
Abaev, Vladimir T.,Dmitriev, Artem S.,Gutnov, Andrey V.,Podelyakin, Sergey A.,Butin, Alexander V.
, p. 1195 - 1204 (2007/10/03)
A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1- ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.
Tricyclic phthalazine derivatives as phosphodiesterase 4 inhibitors
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, (2008/06/13)
Tricyclic phthalazine compounds of formula (I) wherein A is a 5-7 membered heterocycle containing from 1 to 4 nitrogen atoms, optionally partially or totally unsaturated, and optionally substituted by a (C1-4)alkyl group in turn optionally subs
Phthalazine derivatives as phosphodiesterase 4 inhibitors
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, (2008/06/13)
Compounds of formula (I) wherein B is alkylene, amino, CONH or a bond; Cy is optionally substituted phenyl or heteroaryl; R is H, phenyl or (C1-4)alkyl optionally substituted; R1is (C1-6)alkyl or polyfluoro(C1-6)-alkyl; R2is (C4-7)cycloalkyl optionally containing an oxygen atom and optionally substituted; and the N→O derivatives and pharmaceutically acceptable salt thereof are PDE 4 and TNFα inhibitors.
Phthalazine derivatives as phosphodiesterase 4 inhibitors
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Page column 14, (2010/11/30)
The present invention provides a compound selected from the group including: N-3-acetyl-1-(3,5-dichloropyridin-4-ylmethyl)-5-cyclopentyloxy-6-methoxy-4H-phthalazine; 6,7-dimethoxy-1-pyridin-4-ylmethyl-4-thiazol-2-yl-phthalazine; 1-(6,7-dimethoxy-4-pyridin-4-ylmethyl-1H-phthalazin-2-yl)ethanone; 2-methanesulphonyl-6,7-dimethoxy-4-pyridin-4-ylmethyl-1,2-dihydrophthalazine; 2-formyl-6,7-dimethoxy-4-pyridin-4-ylmethyl-1,2-dihydrophthalazine; 1-(6,7-dimethoxy-4-pyridin-4-ylmethyl-1H-phthalazin-2-yl)-1-imidazol-1-ylmethanone; 1-(3,5-dichloro-pyridin-4-ylmethyl)-3-methansulphonyl-6-difluoromethoxy-5-(tetrahydro-furan-2-yloxy)-4H-phthalazine; N→O derivatives thereof; and pharmaceutically acceptable salts thereof. The invention also provides a pharmaceutical composition, which contains a therapeutically effective amount of the above compound in admixture with a pharmaceutically acceptable carrier.
