2903-83-5Relevant academic research and scientific papers
Method for synthesizing phenanthrene compound by using nitroolefin
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Paragraph 0046-0049; 0050-0053; 0054-0057, (2019/03/26)
The invention provides a method for synthesizing a phenanthrene compound. According to the synthesizing method, a 2-phenyl nitroolefin compound as shown in a formula (I) or a 2-thienyl nitroolefin asshown in the formula (II) is used as an initiator for carrying out a reaction at a temperature of 60-100 DEG C for 4-12 hours under the action of an alkaline substance, a silver catalyst, an oxidizingagent and a solvent, and then the corresponding phenanthrene compound as shown in a formula (III) or a formula (IV) is prepared through separation and purification of a reaction liquid. The synthesizing method disclosed by the invention has the characteristics of small harm to the environment, mild reaction conditions, simple and convenient operation, and the like.
Method for synthesizing phenanthrene and derivatives thereof
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Paragraph 0048-0059; 0096-0099, (2019/03/26)
The present invention provides a method for synthesizing phenanthrene and derivatives thereof represented by a formula (III) or (IV). The method is characterized in that a substituted 2-phenylcinnamaldehyde compound represented by a formula (I) or 2-thiophenylcinnamaldehyde represented by a formula (II) is taken as an initial substance, under the effect of a silver catalyst, an oxidant, a basic substance and a solvent, a reaction is carried out at 60 DEG C-100 DEG C for 12-36 hours, the reaction solution is separated and purification is carried out, so that corresponding phenanthrene and derivatives thereof represented by the formula (III) or (IV) are obtained. The synthesis method of the invention has the characteristics of small environmental hazard, mild reaction conditions, simple operation and the like.
A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4 + 2] Annulation of Amino-benzocyclobutenes with Alkynes
Wang, Qile,Zheng, Nan
, p. 4197 - 4201 (2017/06/19)
We report a visible-light-promoted synthesis of substituted naphthalenes via [4 + 2] annulation of amino-benzocyclobutenes with alkynes. Amino-benzocyclobutenes, which are conveniently synthesized by [2 + 2] cycloaddition of arynes with ketenes followed by reductive amination, undergo regioselective opening of the cyclobutenyl ring to reveal a presumably distonic radical cation upon photooxidation by an excited iridium complex. The distonic radical cation undergoes the annulation with terminal and internal alkynes as well as diynes to afford structurally diverse naphthalenes. The regiochemistry of the annulation follows the pattern displayed in the addition of nucleophilic carbon radicals to alkynes. The aniline group plays a dual role in which it not only directs the initial photooxidation to generate the amine radical cation but also serves as a leaving group to complete aromatization.
Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes
Chen, Ming,Zhao, Xinxin,Yang, Chao,Wang, Yanpei,Xia, Wujiong
, p. 12022 - 12026 (2017/03/01)
Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.
Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization
Zhu, Chenghao,Qiu, Lin,Xu, Guangyang,Li, Jian,Sun, Jiangtao
supporting information, p. 12871 - 12875 (2015/09/07)
A highly selective, controllable and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones has been achieved, affording N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported. Basic cyclizations: A highly selective, controllable, and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones affords N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported.
Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds
Xia, Ying,Liu, Zhenxing,Xiao, Qing,Qu, Peiyuan,Ge, Rui,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 5714 - 5717 (2012/07/28)
Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright
Cycloaromatization of α-oxoketene dithioacetals and β-oxodithioacetals with benzyl-,1-(naphthylmethyl) and 2-(naphthylmethyl)magnesium halides: Synthesis of condensed polynuclear aromatic hydrocarbons
Srinivasa Rao,Balu, Maliakel P.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 3499 - 3510 (2007/10/02)
An efficient route for the synthesis of substituted naphthalenes, phenanthrenes and other polynuclear aromatic hydrocarbons has been developed. The methodology involves 1,2- (or sequential 1,4- and 1,2-) addition of either benzyl, 1-(naphthylmethyl) or 2-(naphthylmethyl) magnesium halides to α-oxoketene dithioacetals or β-oxodithioacetals followed by borontrifluoride etherate catalyzed cycloaromatization of the resulting carbinols.
