178817-11-3Relevant articles and documents
Visible-Light-Driven Difluoromethylation of Isocyanides with S-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines
Chen, Jia-Yi,Li, Xin,Lin, Li-Ting,Liu, Guo-Kai,Qin, Wen-Bing,Wong, Henry N. C.,Xiong, Wei
, p. 10479 - 10487 (2020/09/23)
A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic S-(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-c]pyridine, and pyrido[3,4-b]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.
Visible-Light-Induced Decarboxylative Cyclization/Hydrogenation Cascade Reaction to Access Phenanthridin-6-yl(aryl)methanol by an Electron Donor-Acceptor Complex
Shi, Wei,Ma, Fang,Li, Pinhua,Wang, Lei,Miao, Tao
, p. 13808 - 13817 (2020/11/20)
A novel and efficient visible-light-induced decarboxylative cyclization/hydrogenation cascade reaction of α-oxocarboxylic acids and 2-isocyanobiaryls has been developed. Without the need of any external photosensitizer, oxidant, and reductant, this method offers a mild and green approach for the synthesis of diverse alcohols in moderate to good yields. A mechanism indicated that an electron donor-acceptor complex-driven decarboxylation, radical addition/cyclization, and in situ photochemical reduction of ketones to alcohols could be involved in the reaction.
Cobalt(II)-Catalyzed [5+2] C?H Annulation of o-Arylanilines with Alkynes: An Expedient Route to Dibenzo-[b,d]azepines
Ling, Fei,Xie, Zhen,Chen, Jiachen,Ai, Chongren,Shen, Haiwei,Wang, Ze,Yi, Xiao,Zhong, Weihui
supporting information, p. 3094 - 3101 (2019/05/21)
The first example of CoCl2-catalyzed formal [5+2] oxidative annulation of o-arylanilines with alkynes was developed, giving access to various important imine-containing dibenzo-[b,d]azepine scaffolds through sequential C?C/C?N bond formation. The reaction employs catalytic amount of manganese and oxygen as cooxidants, and features a broad substrate scope. Preliminary mechanistic studies suggested that C?H activation is involved in the rate-determining step. Moreover, both internal and terminal alkynes are well tolerated in this transformation. Besides, a regioselective migratory insertion was observed when using terminal alkynes as substrates. (Figure presented.).
Visible Light-Induced Radical Cyclization of Tertiary Bromides with Isonitriles to Construct Trifluoromethylated Quaternary Carbon Center
Wang, Wengui,Guo, Yong,Sun, Ke,Wang, Shoufeng,Zhang, Shuxiang,Liu, Chao,Chen, Qing-Yun
, p. 14588 - 14599 (2018/12/11)
The reaction of trifluoromethylated tertiary bromides with isonitriles induced by visible light is reported. Defluorination was avoided in a radical process. This method provides an efficient approach to compounds containing a trifluoromethylated quaternary carbon center, most of which show excellent potential to be agrochemicals. In addition, the bromides were prepared from perfluoroisobutylene, which is a waste from industry, after several steps. This reaction shows a feasible transfer of harmful waste into useful compounds.
Metal-Oxidant-Free Cobalt-Catalyzed C(sp2)-H Carbonylation of ortho-Arylanilines: An Approach toward Free (NH)-Phenanthridinones
Ling, Fei,Zhang, Chaowei,Ai, Chongren,Lv, Yaping,Zhong, Weihui
, p. 5698 - 5706 (2018/05/23)
A traceless directing group assisted Co-catalyzed C(sp2)-H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C-H bond cleavage probably occurred in the rate-determining step.
Visible-light-mediated radical insertion/cyclization cascade reaction: Synthesis of phenanthridines and isoquinolines from isocyanides
Feng, Shangbiao,Li, Tao,Du, Chenglong,Chen, Peng,Song, Dengpeng,Li, Jinlai,Xie, Xingang,She, Xuegong
supporting information, p. 4585 - 4588 (2017/04/28)
A visible-light promoted single electron oxidation of ether enabled by photoredox catalysis has been accomplished. This procedure initiates a novel radical insertion/cyclization cascade reaction to generate phenanthridines and isoquinolines from easily available isocyanides under mild reaction conditions.
Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis
Rong, Jian,Deng, Ling,Tan, Ping,Ni, Chuanfa,Gu, Yucheng,Hu, Jinbo
supporting information, p. 2743 - 2747 (2016/02/26)
The radical fluoroalkylation of isocyanides with fluorinated sulfones is enabled by visible-light photoredox catalysis. A wide range of readily available mono-, di-, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a new route to fluoroalkyl radicals.
Terphenyl cyclooxygenase-2 (COX-2) inhibitors: Optimization of the central ring and o-biphenyl analogs
Pinto, Donald J. P.,Batt, Douglas G.,Pitts, William J.,Petraitis, Joseph J.,Orwat, Michael J.,Wang, Shuaige,Jetter, James W.,Sherk, Susan R.,Houghton, Gregory C.,Copeland, Robert A.,Covington, Maryanne B.,Trzaskos, James M.,Magolda, Ronald L.
, p. 919 - 924 (2007/10/03)
The discovery of terphehyl derivatives as highly selective COX-2 inhibitors resulted from our efforts to overcome poor pharmacokinetics demonstrated by the COX-2 selective diarylthiophene DuP 697 [2-bromo-4-(4'- sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene]. Detailed SAR related to the ortho-biphenyls and variants of the central ring are described herein.
Prostaglandin synthase inhibitors
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, (2008/06/13)
This invention relates to ortho substituted phenyl compounds as inhibitors of prostaglandin synthase, to pharmaceutical compositions comprising such compounds and to methods of using such compounds as antiinflammatory and antipyretic agents. The class of compounds useful in this method of treatment is represented by Formula I below: STR1
