- Dynamic equilibrium of self-assembled cyclic trimer and tetramer of 1-methyl-5-imidazolylcobalt(III)porhyrin
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Dynamic equilibrium of self-assembled multi-porphyrin systems is of interest in obtaining switchable photoresponsive material, but rarely reported. 1-methyl-5-imidazolylcobalt(III)porphyrin (1Co) synthesized here assembled automatically into cyclic trimer and tetramer by intermolecular imidazolyl-cobalt(III) coordination. The trimer-tetramer equilibrium was dependent on concentration and solvent, as examined by NMR spectrometry. In CDCl3, the tetramer formation was favored at high concentrations, as the ratio of the trimer to the tetramer was 1:2 at 14.8 mM 1Co, and shifted to 1:8 at 74 mM. Further, when the sample was concentrated from a CHCl3 solution to dryness, the ratio increased to 1:24 on dissolution. In CD 3OD, on the other hand, only the trimer was observed in the wide concentration range. Accordingly, both the trimeric and the tetrameric structures could be prepared selectively by the choice of concentration and solvent.
- Tanaka, Akira,Ryuno, Aya,Okada, Saori,Satake, Akiharu,Kobuke, Yoshiaki
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- Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling
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A variety of 2-substituted 5-alkynyl-1H-imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1,2-dimethyl-1H-imidazole, 2-chloro-1-methyl-1H-imidazole, and 2-aryl-1-methyl-1H-imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation.
- Bellina, Fabio,Lessi, Marco,Marianetti, Giulia,Panattoni, Alessandro
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supporting information
p. 3855 - 3857
(2015/06/08)
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- A novel series of IKKβ inhibitors part II: Description of a potent and pharmacologically active series of analogs
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A novel series of (E)-1-((2-(1-methyl-1H-imidazol-5-yl) quinolin-4-yl) methylene) thiosemicarbazides was discovered as potent inhibitors of IKKβ. In this Letter we document our efforts at further optimization of this series, culminating in 2 with submicromolar potency in a HWB assay and efficacy in a CIA mouse model.
- Cushing, Timothy D.,Baichwal, Vijay,Berry, Karen,Billedeau, Roland,Bordunov, Viola,Broka, Chris,Browner, Michelle F.,Cardozo, Mario,Cheng, Peng,Clark, David,Dalrymple, Stacie,Degraffenreid, Michael,Gill, Adrian,Hao, Xiaolin,Hawley, Ronald C.,He, Xiao,Labadie, Sharada S.,Labelle, Marc,Lehel, Csaba,Lu, Pu-Ping,McIntosh, Joel,Miao, Shichang,Parast, Camran,Shin, Youngsook,Sjogren, Eric B.,Smith, Marie-Louise,Talamas, Francisco X.,Tonn, George,Walker, Keith M.,Walker, Nigel P.C.,Wesche, Holger,Whitehead, Chris,Wright, Matt,Jaen, Juan C.
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scheme or table
p. 423 - 426
(2011/02/27)
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- Cross-coupling methods for the large-scale preparation of an imidazole - Thienopyridine: Synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl] -(2-methyl-1H-indol-5-yl)-amine
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The multihundred-gram synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl] -(2-methyl-1H-indol-5-yl)-amine (1) is described utilizing a Stille cross-coupling of an iodothienopyridine (3) with 5-(tributylstannyl)-1-methylimidazole (11). Several cross-coupling methods were evaluated for the conversion of thienopyridine 3 to imidazole - thienopyridine 2, but only two were effective: the Stille coupling and a Negishi cross-coupling of the organozinc reagent derived from 2-(tertbutyldimethylsilyl)-1-methylimidazole and iodothienopyridine (3). The latter procedure worked well on laboratory scale (50 g), but was capricious upon scale-up. The issues with scale-up of an organostannane reagent are discussed, including control and analysis of organotin levels.
- Ragan,Raggon,Hill,Jones,McDermott,Munchhof,Marx,Casavant,Cooper,Doty,Lu
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p. 676 - 683
(2013/09/05)
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- Studies on β-lactam antibiotics, synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs
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The synthesis and biological activity of the novel series of 1β-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-I stability. The best compound in this series, FR21818 (1a) displayed ex
- Azami, Hidenori,Barrett, David,Tanaka, Akira,Sasaki, Hiroshi,Matsuda, Keiji,Sakurai, Minora,Matsumoto, Yoshimi,Tawara, Shuichi,Chiba, Toshiyuki,Sakane, Kazuo
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p. 1409 - 1414
(2007/10/03)
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- The use of vinyl imidazoles as Diels-Alder dienes
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The first use of a vinylimidazole as a Diels-Alder diene is reported. Semiempirical calculations are used to characterize 1-methyl-5-vinylimidazole as an electron-rich diene
- Walters, Michael A.,Lee, Melissa D.
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p. 8307 - 8310
(2007/10/02)
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