22115-41-9Relevant articles and documents
Double elimination protocol for synthesis of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene
Orita, Akihiro,Hasegawa, Daiki,Nakano, Takehiko,Otera, Junzo
, p. 2000 - 2004 (2002)
A new method for constructing 5,6,11,12-tetradehydrodibenzo[a,e]-cyclooctene is described on the basis of one-pot double elimination protocol. The target molecule, which is the smallest cyclophane with alternate arylene-]ethynylene linkage, is synthesized in 61% yield through oxidative dimerization of ortho-(phenylsulfonylmethyl)-benzaldehyde. The initial carbon-carbon bond formation between sp3 carbons followed by stepwise conversion to sp2 and finally sp carbons bypasses the difficulty encountered in direct coupling of the sp carbon in the terminal acetylene. The mechanism of this process is discussed. The Wittig-Horner-type coupling is a key reaction employed for the carbon-carbon bond formation. Generation of (E)-vinylsulfone moiety in the first coupling between a-sulfonyl anion and aldehyde functions is crucial for the effective second coupling to complete the cyclization. The syn-elimination of the (E)-vinylsulfone moieties in the cyclized intermediate furnishes the acetylenic bonds.
DICYANSTYRYL BENZENE DERIVATIVES AND FLUORESCENT MATERIAL COMPRISING THE SAME
-
Paragraph 0227; 0232-0235, (2019/06/13)
The present invention refers to die [...] benzene derivatives represented by formula 1 are disclosed. The, head of the present invention die [...] benzene to yield fluorescent derivatives (Dicyanstyryl benzene) to minimize environmental pollution by reducing the drain diameter number fluorescent material can be [...] number can be improve. [Formula 1] (by machine translation)
Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles
Ai, Wenying,Liu, Yaqian,Wang, Qian,Lu, Zhonglin,Liu, Qiang
, p. 409 - 412 (2018/01/27)
A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.
Synthetic method of 2-cyanobenzyl bromide and analogues thereof
-
, (2017/08/30)
The invention discloses a synthetic method of 2-cyanobenzyl bromide and analogues thereof. The synthetic method comprises the following steps: 1) using a compound I as a raw material, conducting reaction on the compound I and tert-butyldimethylsilyl chloride, and adding a first solvent and an acid-binding agent to generate a compound II; 2) dissolving the compound II into a second solvent, adding a palladium catalyst and a cyaniding agent, and carrying out a cyaniding reaction to generate a compound III; 3) dissolving the compound III into a third solvent without taking off protecting groups, and directly carrying out a bromination reaction under the effect of phosphorus tribromide so as to prepare a compound IV. The synthetic method is simple in process route and relatively high in product quality and yield.
Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes
Xu, Feng,Peng, Lifen,Shinohara, Kenta,Morita, Takamoto,Yoshida, Suguru,Hosoya, Takamitsu,Orita, Akihiro,Otera, Junzo
, p. 11592 - 11608 (2015/01/09)
Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.
Synthesis, optical and nonlinear optical properties of new pyrazoline derivatives
Mysliwiec,Szukalski,Sznitko,Miniewicz,Haupa,Zygadlo,Matczyszyn,Olesiak-Banska,Samoc
, p. 63 - 70 (2013/12/04)
We report on synthesis and optical properties of new organic compounds based on substituted pyrazole ring. The investigated pyrazoline derivatives (PRDs) exhibit efficient broadband photoluminescence which covers nearly whole visible spectrum. The experimental results are compared to quantum chemical calculations. Amplified spontaneous emission and photodegradation measurements were performed for hybrid systems based on selected PRDs doped into poly(methyl methacrylate) matrix proving the potential utility of such systems in lasing applications. Two-photon absorption (TPA) properties were characterized by the femtosecond Z-scan technique.
Rhodium(iii)-catalyzed olefinic C-H alkynylation of enamides at room temperature
Feng, Chao,Feng, Daming,Loh, Teck-Peng
supporting information, p. 9865 - 9868 (2014/08/18)
Rh(iii)-catalyzed C-H olefinic alkynylation of enamides for the stereospecific construction of synthetically useful Z-type enynamides is reported. This protocol displays good functionality tolerance and operational simplicity thus providing an alternative synthetic opportunity for the ease of access to specific 1,3-enyne derivatives.
Photochemical and thermal intramolecular 1,3-dipolar cycloaddition reactions of new o-stilbenemethylene-3-sydnones and their synthesis
Butkovic, Kristina,Marinic, Zeljko,Molcanov, Kresimir,Kojic-Prodic, Biserka,Sindler-Kulyk, Marija
supporting information; experimental part, p. 1663 - 1670 (2012/02/04)
New trans-and cis-o-stilbene-methylene-sydnones 3a,b were synthesized by transforming the trans-and cis-o-aminomethylstilbene derivative, obtained by reduction of corresponding o-cyano derivatives, into glycine ester derivatives (43 and 31% yield) followed by hydrolysis (90 and 96% yield), nitrosation and ring closure with acetic acid anhydride (30 and 40% yield). The products were submitted to photochemical and thermal intramolecular [3 + 2] cycloadditions to afford diverse heteropolycyclic compounds. Photochemical reactions afforded cis-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (11, 12.5% yield) and trans-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (12, 5% yield). Thermal reactions afforded 3-(4-methylphenyl)-3,3a,8,8a- tetrahydroindeno[2,1-c]pyrazole (14, 50% yield) and 11-(4-methylphenyl)-9,10- diazatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene (15, 22% yield).
(1,4-DIAZA-BICYCLO[3.2.2]NON-6-EN-4-YL)-HETEROCYCLYL-METHANONE LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, USEFUL FOR THE TREATMENT OF DISEASE
-
Page/Page column 61; 62, (2009/05/30)
The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds, which act as ligands for the a7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof. The novel compounds include compounds of formula I: (I) wherein X, R1, and R2 are as herein defined.
4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors of the checkpoint kinase Wee1. structure-activity relationships for chromophore modification and phenyl ring substitution
Palmer, Brian D.,Thompson, Andrew M.,Booth, R. John,Dobrusin, Ellen M.,Kraker, Alan J.,Lee, Ho H.,Lunney, Elizabeth A.,Mitchell, Lorna H.,Ortwine, Daniel F.,Smaill, Jeff B.,Swan, Leesa M.,Denny, William A.
, p. 4896 - 4911 (2007/10/03)
High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]-carbazole-1,3(2H,6H)- dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.
