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Chung JY Cvetovich RJ McLaughlin M Amato J Tsay FR Jensen M Weissman S Zewge D 《The Journal of organic chemistry》2006,71(22):8602-8609
Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl)magnesium chloride to a naphthyridone N-oxide. The N-oxide exerted complete chemoselectivity via chelation in directing the Grignard addition to the alpha position as opposed to 1,4-addition on the ene-lactam. The dihydropyridyl adduct was in situ aromatized with isobutylchloroformate followed by heating in pyridine. Syntheses of Grignard precursor, N-tert-butyl-4-chloro-piperidine, were accomplished via transamination with a quaternary ammonium piperidone or via addition of methylmagnesium chloride to an iminium ion. Utilizing this chemistry, multi-kilogram preparation of compound 1 was successfully demonstrated. 相似文献
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Watson William H. Kashyap Ram P. Krawiec Mariusz Marchand Alan P. Tsay Fuh-Rong 《Structural chemistry》1994,5(1):21-35
5-Methyl-2-phenylpentacyclo[5.4.0.02, 6.03, 10.05, 9]undecane-8, 11-dione,5-methyl-2-phenylpentacyclo [5.4.0.02,6.03,10.05,9]undecane-8-one-11-ol,and 5-methyl-2-phenylpentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-diol are three cage compounds which differ only in the oxidation state at C(8) and C(11). The three compounds contain a four-membered, a six-membered, and four five-membered rings fused into a cagelike structure. An X-ray structure analysis shows the C(1)-C(7) and C(9)-C(10) bonds in the diketo cage to be 1.606(2) and 1.586(2) Å, which are significantly longer than in the other two molecules. In order to assess the effects of strain, steric, and electronic factors in these compounds, we investigated the unsubstituted parent cage compounds and a series of derivatives by molecular mechanics (MM3), AMPAC (AM1), MOPAC (PM3), and GAUSSIAN 90 calculations. These data suggest that dipolar through space interactions are responsible for the bond elongation and not a
–
* interaction, which has been postulated in parallel-systems originating from a common bond. A small degree of
–
* through-bond interaction may contribute to the lengthening in the dimethylene cage analogues. 相似文献
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A straightforward synthesis of substituted polythiophene-fused-3-sulfolenes from the readily prepared methyl 3-hydroxy-4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate will be presented. Upon thermolysis in the presence of N-phenylmaleimide, these new substrates serve as precursors of reactive polythiophene o-quinodimethanes to give the corresponding Diels-Alder adducts in high yields. 相似文献
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Tidal Effects on Groundwater Motions 总被引:1,自引:0,他引:1
Assuming a sharp interface between freshwater and seawater within a coastal aquifer, a theory is developed to account for the piezometric head movement of steady and unsteady components in terms of large- and small-time scales. Tidal fluctuations are simulated by a series of decomposed simple harmonic motions in time. Groundwater fluctuation induced by tidal motion is perturbed to the groundwater head of large-time scale. Ghyben–Herzberg formulation is applied for solutions of large-time scale and a unified formulation for various flows of small-time scale is derived (Strack, 1989). Approximate analytical solutions for amplitudes and phase lags of tidal groundwater motions and the freshwater–seawater interface for a coastal aquifer in a circular island are obtained. The induced fluctuation amplitude generally decays in distance with a parameter consisting of hydraulic conductivity, storage coefficient, thickness of aquifer and tidal period. The present approach can be applied to confined and unconfined aquifers, with only freshwater flows or interfacial flows. The theory is verified with some experimental results (Parlange, et al., 1984; Nielson, 1990). It can also used to determine physical parameters of an aquifer by monitoring the groundwater fluctuations due to tidal motions (Carr and van der Kamp, 1969). 相似文献