- A novel one-step conversion of 3,3,3-Triphenylpropionic acid to 10- cyano-10-phenyl-9-anthrone
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3,3,3-Triphenylpropionic acid transformed to 10-cyano-10-phenyl-9- anthrone when it was treated in consecutive order with trifluoroacetic anhydride and sodium nitrite in trifluoroacetic acid.
- Smushkevich,Smushkevich,Kislitsin
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- Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone-Thioimidazolidine-Oxindoles
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This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone-thioimidazolidine-oxindoles bearing two adjacent spiro-quaternary stereocenters in good to excellent yields with excellent diastereo- and enantioselectivities. Versatile transformations of the products into other potential bioactive bispirocyclic heterocycles have also been demonstrated.
- Zhao, Bo-Liang,Du, Da-Ming
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- Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones
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A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient
- Du, Da-Ming,Hou, Xi-Qiang,Wen, Jiang-Bo,Yan, Li
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- Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation
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(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.
- Nguyen, Thi Ha,Ma, Eunsook
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supporting information
p. 3717 - 3728
(2021/11/01)
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- Synthesis of 2-(Cyanomethyl)benzoic Esters via Carbon-Carbon Bond Cleavage of Indanones
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A novel synthesis of 2-(cyanomethyl)benzoic esters from indanone derivatives has been established. This reaction proceeds via a deprotonation of alcohols with a chemical base, followed by a nucleophilic addition to indanones and Beckmann fragmentation. In addition, this reaction could also work under electrochemical conditions, and no external chemical bases were needed. This mild method offers a novel strategy for the late-stage functionalization of various natural alcohols.
- Meng, Xiangtai,Chen, Dengfeng,Liu, Rui,Jiang, Ping,Huang, Shenlin
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p. 10852 - 10860
(2021/08/20)
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- Cu-catalyzed coupling of indanone oxime acetates with thiols to 2,3-difunctionalized indenones
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A Cu-catalyzed coupling reaction of indanone oxime acetates with thiols has been developed for the synthesis of 2,3-functionalized 1-indenones. This protocol has several features including easy mild reaction conditions, stabilized enamine products, good t
- Fu, Yuanyuan,Zhao, Xueyan,Chen, Dengfeng,Luo, Jinyue,Huang, Shenlin
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supporting information
p. 10719 - 10722
(2021/10/20)
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- Preparation method of 2-aminoindan derivative
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The invention discloses a preparation method of a 2-aminoindan derivative. The preparation method comprises the following steps: with a 1-indanone derivative as a starting raw material, carrying out oximation reaction, and synchronously reducing carbonyl and hydroxyl oxime under the catalysis of Lewis acid such as aluminum chloride in the presence of a boron metal reducing agent, so as to obtain the 2-aminoindan derivative. The invention further provides the 2-aminoindan derivative prepared by virtue of a synthetic method and a corresponding intermediate derivative. Compared with a synthetic method of the 2-aminoindan derivative in the prior art, the synthetic method disclosed by the invention has the beneficial effects that (1) only two reaction steps are adopted, and the reaction steps are obviously less than the reaction steps in the prior art; (2) the cost is relatively low, the operation is simple and convenient, and the yield is high; and (3) the preparation method is suitable for large-scale industrial production and has relatively good application prospects.
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Paragraph 0023; 0024; 0025; 0026
(2019/03/08)
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- Rapid Construction of Complex 2-Pyrrolines through Lewis Acid-Catalyzed, Sequential Three-Component Reactions via in Situ-Generated 1-Azaallyl Cations
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The first Sc(OTf)3-catalyzed dehydration of 2-hydroxy oxime ethers to generate benzylic stabilized 1-azaallyl cations, which are captured by 1,3-carbonyls, is described. A subsequent addition of primary amines in a sequential three-component re
- Schlegel, Marcel,Schneider, Christoph
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supporting information
p. 3119 - 3123
(2018/05/28)
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- INDOLAMID DERIVATIVES WHICH POSSESS GLYCOGENPHOSPHORYLASE INHIBITORY ACTIVITY
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Heterocyclic amides of formula (1) wherein: is a single or double bond;A is phenylene or heteroarylene;m is 0, 1 or 2;n is 0, 1 or 2;R1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; r is 1 or 2; Y is -NR2R3 or -OR3;R2 and R3 are selected from for example hydrogen, hydroxy, aryl, heterocyclyl and C 1-4 alkyl(optionally substituted by 1 or 2 R8 groups);R4 is selected from for example hydrogen, halo, nitro, cyano, hydroxy, C 1-4 alkyl, and C 1-4 alkanoyl; R8 is selected from for example hydroxy, -COCOOR9, -C(O)N(R9)(R10), -NHC(O)R9 , (R9)(R10)N- and -COOR9 ;R9 and R10 are selected from for example hydrogen, hydroxy, C 1-4 alkyl (optionally substituted by 1 or 2 R13 );R13 is selected from hydroxy, halo, trihalomethyl and C 1-4 alkoxy;or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.
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Page/Page column 70
(2008/06/13)
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- Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors
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Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR4═CR5—, —CR4═CR5—S—, —O—CR4═CR5—, —CR4═CR5—O—, —N═CR4—S—, —S—CR4═N—, —NR6—CR4═CR5— and —CR4═CR5—NR6—; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.
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- Syntheses and Photophysical Properties of Some 5(2)-Aryl-2(5)-(4-pyridyl)oxazoles and Related Oxadiazoles and Furans
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A number of 5-aryl-2-(4-pyridyl)oxazoles, a 2-aryl-5-(4-pyridyl)oxazole, the related oxadiazole and furan, several 2-(4-pyridyl)cycloalkanooxazoles, and many of their quaternary salts were prepared.No single standard synthesis was effective for preparation of more than a few of the 25 free bases described; methods often unique to a base were employed.Minor variations in structure sometimes produced large differences in absorption and emission wavelengths, as well as in the magnitude of the extinction coefficient.The salts are of interest as laser dyes, scintillation fluors, biological stains, and shifters for luminescent solar concentrators.
- Hall, J. Herbert,Chien, Joseph Yuming,Kauffman, Joel M.,Litak, Peter T.,Adams, Jeffrey K.,et al.
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p. 1245 - 1273
(2007/10/02)
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