- In(III)-Catalyzed Direct Regioselective Syntheses of 1-Naphthaldehyde Derivatives via a Hidden Aldehyde 1,3-Translocation and Disjointed CO2Extrusion
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A highly regioselective annulation of 3-formylchromones with alkynes in the presence of indium triflate leads to the direct construction of diverse 1-naphthaldehyde derivatives. This one-pot de novo protocol features an unusual aldehyde 1,3-translocation and disjointed CO2 extrusion. This methodology is effective for the construction of structurally diverse 1-naphthaldehydes bearing chiral moieties and polyaromatics. These naphthaldehydes can be further easily elaborated into a wide variety of functional groups. Density functional theory computations show that this In(III)-catalyzed reaction appears to proceed via a stepwise dearomative cyclization, lactonization, ring contraction, and, finally, extrusion of CO2. Most interestingly, the aldehyde translocation occurs not by the transposition of the aldehyde but rather by the skeletal rearrangement of the substrate arene.
- Sultana, Sabera,González-Montiel, Gisela A.,Pradhan, Samjhana,Khanal, Hari Datta,Nale, Sagar D.,Cheong, Paul Ha-Yeon,Lee, Yong Rok
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- Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C?H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes
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Described herein is the synthesis of stable oxonium-doped polycyclic aromatic hydrocarbons (PAHs) by the rhodium-catalyzed C?H activation/annulations of naphthalene-type aldehydes with internal alkynes. This protocol provides four divergent reaction types, including two unexpected annulations with an oxygen transposition process, which lead to diverse types of phenalenyl-fused pyrylium cations comprising a four-, five-, or six-ring-fused π-conjugated core. The annulations exhibit an exquisite regioselectivity and a high tolerance of sensitive functional groups. These PAHs feature intriguing photophysical properties such as full-color tunable fluorescence emission, high quantum yield, and positively charged core, and can be reduced easily to the phenalenyl radicals.
- Yin, Jiangliang,Tan, Meiling,Wu, Di,Jiang, Ruyong,Li, Chengming,You, Jingsong
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- Palladium-Catalyzed Regiospecific peri- And ortho-C-H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups
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An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without pre- and postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C-H bond cleavage played a crucial role during the reaction process.
- Hu, Lihong,Jiang, Jing,Lin, Yaoyu,Ma, Congzhe,Song, Wanbin,Yuan, Dandan,Zhang, Yinan
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supporting information
p. 279 - 284
(2021/01/13)
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- Identification of C5-NH2 Modified Oseltamivir Derivatives as Novel Influenza Neuraminidase Inhibitors with Highly Improved Antiviral Activities and Favorable Druggability
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Our previous efforts have proved that modifications targeting the 150-cavity of influenza neuraminidase can achieve more potent and more selective inhibitors. In this work, four subseries of C5-NH2 modified oseltamivir derivatives were designed
- Bertagnin, Chiara,Du, Ruikun,Guizzo, Laura,Hou, Lingxin,Huang, Bing,Jia, Ruifang,Ju, Han,Kang, Dongwei,Kong, Xiujie,Li, Ping,Liu, Xinyong,Loregian, Arianna,Ma, Xiuli,Murugan, N. Arul,Poongavanam, Vasanthanathan,Zhan, Peng,Zhang, Ying
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p. 17992 - 18009
(2021/11/18)
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- 2-[(arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding
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The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs wit
- Bair,Andrews,Tuttle,Knick,Cory,McKee
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p. 1983 - 1990
(2007/10/02)
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