- Diastereomers of a cofacial ternaphthalene and two azaternaphthalenes. Syntheses and barriers to isomerization
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The title compounds, a mixture of anti and syn diastereomers, were prepared by Pd-catalyzed coupling of areneboronic acids with hetaryl halides. Energy barriers for the interconversion of the diastereomers obtained by kinetic and computational studies show a dependence on the location of the annular nitrogen atom, the ortho providing a smaller barrier than the meta nitrogen atom.
- Zoltewicz, John A.,Maier, Norbert M.,Lavieri, Sophie,Ghiviriga, Ion,Abboud, Khalil A.,Fabian, Walter M. F.
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Read Online
- Identification of New FLT3 Inhibitors That Potently Inhibit AML Cell Lines via an Azo Click-It/Staple-It Approach
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Acute myeloid leukemia (AML) is an aggressive malignancy with only a handful of therapeutic options. About 30% of AML patients harbor mutated FLT3 kinase, and thus, this cancer-driver has become a hotly pursued AML target. Herein we report a new class of FLT3 inhibitors, which potently inhibit the proliferation of acute myeloid leukemia (AML) cells at nanomolar concentrations.
- Ma, Xiaochu,Zhou, Jie,Wang, Changhao,Carter-Cooper, Brandon,Yang, Fan,Larocque, Elizabeth,Fine, Jonathan,Tsuji, Genichiro,Chopra, Gaurav,Lapidus, Rena G.,Sintim, Herman O.
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Read Online
- Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts
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The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.
- Tang, Juan,Chen, Xue,Zhao, Chao-Qun,Li, Wen-Jing,Li, Shun,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua
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p. 716 - 730
(2020/12/22)
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- Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature
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A halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its importance in lowering the activation barrier for this reaction, the presence of radical intermediates in a reaction mixture, and the regioselectivity of the reaction have been demonstrated with several control experiments, spectroscopic analysis, and quantum chemical calculations. Allowing the formation of the halogen bond may offer a new strategy to generate the reactive radical intermediates and to enable the otherwise elusive electron-catalyzed reactions under mild reaction conditions.
- Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
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supporting information
p. 6642 - 6654
(2019/06/14)
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- I2/TBHP mediated multiple C[sbnd]H bonds functionalization of azaarenes with methylarenes to synthesize iodoisoquinolinones via iodination/N-benzylation/amidation sequence
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An oxidative multi-functionalization of azaarenes with benzylic C[sbnd]H bonds of methylarenes via iodination/N-benzylation/amidation cascade, to produce N-benzyl-4-iodoisoquinolin-1(2H)-ones and N-benzyl-3-iodoquinolin-2(1H)-ones is developed. The molecular iodine plays a triple role in activating benzylic sp3 C[sbnd]H bond of methylbenzenes, accelerating the oxidation process and serving as iodination reagent. This reaction utilizes cheap and readily available azaarenes and methylarenes as starting materials and proceeds under metal-free conditions to construct C-I, C[sbnd]N and C[dbnd]O bonds consecutively and afford iodo(iso)quinolinones efficiently.
- Luo, Wen-Kun,Xu, Cong-Ling,Yang, Luo
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supporting information
(2019/11/28)
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- Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
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The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.
- Li, Lu,Liu, Wenbo,Zeng, Huiying,Mu, Xiaoyue,Cosa, Gonzalo,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 8328 - 8331
(2015/07/15)
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- Metal-free synthesis of N-fused heterocyclic iodides via C-H functionalization mediated by tert-butylhydroperoxide
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Direct, regioselective and metal-free synthesis of fused N-heterocyclic iodides is reported. This regioselective C-H functionalization is mediated by tert-butylhydroperoxide (TBHP), via dual activation of molecular iodine and a heterocyclic substrate, resulting in the in situ generation of electrophilic iodine species (I+), and free radical(s) tBuO? or tBuOO?, driving the iodination reaction.
- Sharma, Krishna K.,Patel, Dhananjay I.,Jain, Rahul
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supporting information
p. 15129 - 15132
(2015/10/12)
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- Regioselective, Molecular Iodine-Mediated C3 Iodination of Quinolines
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A novel and convenient method has been developed for the regioselective iodination of quinolines at their C3 position under metal-free conditions. Iodinated quinolines, which are popular building blocks in organic and medicinal chemistry, can be prepared in gram quantities and good yields using this method and further derivatized to give increasingly complex compounds. Preliminary mechanistic studies have shown that this reaction most likely occurs via a radical intermediate.
- Sun, Kai,Lv, Yunhe,Wang, Junjie,Sun, Jingjing,Liu, Lulu,Jia, Mingyang,Liu, Xin,Li, Zhenduo,Wang, Xin
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supporting information
p. 4408 - 4411
(2015/09/28)
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- The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil
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A radical based direct C-H iodination protocol for quinolines, quinolones, pyridones, pyridines, and uracil has been developed. The iodination occurs in a C3 selective manner for quinolines and quinolones. Pyridones and pyridines undergo C3 and C5 iodination, while dimethyl uracil undergoes C5 iodination. Scope of the method was demonstrated through the rapid synthesis of both electron rich as well as electron poor heteroaromatic iodides. The protocol was found to be scalable and general, while a mechanism has been proposed.
- Dutta, Uttam,Deb, Arghya,Lupton, David W.,Maiti, Debabrata
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supporting information
p. 17744 - 17747
(2015/12/18)
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- Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation
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A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.
- Partridge, Benjamin M.,Hartwig, John F.
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supporting information
p. 140 - 143
(2013/03/28)
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- On the synthesis of arylpropiolic acids and investigations towards the formation of vinyl chlorides by HCl addition during esterification reactions
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The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl2 was examined. Georg Thieme Verlag Stuttgart New York.
- Hapke, Marko,Kral, Karolin,Spannenberg, Anke
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experimental part
p. 642 - 652
(2011/04/15)
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- NOVEL COMPOUNDS AS PHARMACEUTICAL AGENTS
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The current invention relates to compounds of the formula:(Ia) and the pharmaceutically acceptable salts thereof and their use as TGF-beta signal transduction inhibitors for treating cancer and other diseases in a patient in need thereof by administration of said compounds.
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- Studies on Organometallic Compounds. II. Facile and Convenient Method for the Synthesis of Idoazines through Iododestannation of Trimethylstannylazines
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Trimethylsatannyl and bis(trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethylsatannane and sodium.These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.Keywords -trimethylsannylazine; bis(trimethylstannyl)azine; iodoazine; diiodoazine; iododestannation; trimethylstannyl sodium; chlorotrimethylstannane
- Yamamoto, Yukata,Yanagi, Akihiko
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p. 1731 - 1737
(2007/10/02)
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