- Magnesiate-Utilized/Benzyne-Mediated Approach to Indenopyridones from 2-Pyridones: An Attempt to Synthesize the Indenopyridine Core of Haouamine
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An efficient, short-staged synthesis of cis-fused indeno[2,1-b]- and indeno[1,2-c]pyridin-2-ones, starting from 2-pyridones, using magnesiates of type R3MgLi as nucleophilic and deprotonation agents, mediated by benzyne generated in situ, under optimized conditions, is described. Following the developed protocol, rare C4a-arylsubstituted indeno[2,1-b]pyridones, resembling the core of haouamine, were obtained. The protocol offering the one-pot synthesis directly from 2-pyridone is also described.
- Idzik, Tomasz J.,Borzyszkowska-Ledwig, Aleksandra,Struk, ?ukasz,So?nicki, Jacek G.
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supporting information
p. 9667 - 9671
(2019/11/29)
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- Facile Route to 2-Fluoropyridines via 2-Pyridyltrialkylammonium Salts Prepared from Pyridine N-Oxides and Application to 18F-Labeling
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Among known precursors for 2-[18F]fluoropyridines, pyridyltrialkylammonium salts have shown excellent reactivity; however, their broader utility has been limited because synthetic methods for their preparation suffer from poor functional group
- Xiong, Hui,Hoye, Adam T.,Fan, Kuo-Hsien,Li, Ximin,Clemens, Jennifer,Horchler, Carey L.,Lim, Nathaniel C.,Attardo, Giorgio
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p. 3726 - 3729
(2015/08/18)
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- ORGANIC COMPOUNDS
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The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.
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Page/Page column 17
(2009/07/03)
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- 8-Azabicyclo[3.2.1]octane derivatives
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The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein each of the substituents is given the definition as set forth in the specification and claims, or a pharmaceutically acceptable salt thereof or solvate thereof. The present invention also relates to a pharmaceutical composition comprising an 8-azabicyclo[3.2.1]octane derivative in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of the 8-azabicyclo[3.2.1]octane derivative in therapy.
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Page/Page column 9
(2008/06/13)
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- 8-AZABICYCLO[3.2.1]OCTANE DERIVATIVES USEFUL AS MONOAMINE REUPTAKE INHIBITORS
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The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein R1 is H or C1-5alkyl; Y is O, S or O(CH2)m; m is 1 or 2; n is 0 or 1; Ar1 is phenylene or pyridylene, said phenylene and pyridylene being 1,3-linked with respect to O and when n is 1 with Y and when n is 0 with Ar2, said phenylene or pyridylene being optionally substituted with one or two substituents independently selected from halogen, C1-5alkyl, C1-5alkoxy, C3-6cycloalkyl, C2-5alkenyl, C2-5alkynyl, phenyl, CN and hydroxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein the oxygen of said hydroxy is optionally bonded to Ar2 to form a 5-membered ring; Ar2 is phenyl or a 5-6 membered heteroaryl, said phenyl or 5-6 membered heteroaryl being optionally substituted with one to three substituents independently selected from halogen, C1-5alkyl, C1-5alkoxy, CN, CONR2R3, CO2R4, NHCOR5 and hydroxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein the oxygen of said hydroxy is optionally bonded to Ar1 to form a 5-membered ring; R2-R4 are independently H or C1-5alkyl and R5 is C1-5alkyl, or a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutical composition comprising a 8- azabicyclo[3.2.1]octane derivative according to the present invention in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of a 8- azabicyclo[3.2.1]octane derivative according to the present invention in therapy.
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Page/Page column 20
(2010/11/27)
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- Synthesis and SAR of highly potent and selective dopamine D 3-receptor antagonists: Variations on the 1H-pyrimidin-2-one theme
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In our efforts to further pursue one of the most selective dopamine D 3-receptor antagonists reported to date, we now describe the synthesis and SAR of novel and highly selective dopamine D3 antagonists based on a 1H-pyridin-2-one or
- Geneste, Herve,Amberg, Wilhelm,Backfisch, Gisela,Beyerbach, Armin,Braje, Wilfried M.,Delzer, Juergen,Haupt, Andreas,Hutchins, Charles W.,King, Linda L.,Sauer, Daryl R.,Unger, Liliane,Wernet, Wolfgang
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p. 1934 - 1937
(2007/10/03)
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- 2-Pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B
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The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).
- Carles, Lionel,Narkunan, Kesavaram,Penlou, Sebastien,Rousset, Laurence,Bouchu, Denis,Ciufolini, Marco A.
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p. 4304 - 4308
(2007/10/03)
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- Convenient synthesis and transformation of 2,6-dichloro-4-iodopyridine
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(Matrix Presented) We describe a convenient scalable synthesis of 2,6-dichloro-4-iodopyridine and demonstrate its utility by stepwise elaboration to a number of 2,4,6-trisubstituted pyridines.
- Mello, Jesse V.,Finney, Nathaniel S.
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p. 4263 - 4265
(2007/10/03)
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- 2-Oxo-1,2-(dihydropyridyl)-2H-1-benzopyrans
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The present invention is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof: STR1 wherein Y, R2, R3, R4, R5, R6, R7 , a and b are as defined in the Specifica
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- PHOTOCHEMISTRY OF PYRIDINE N-OXIDES. TRAPPING OF AN INTERMEDIATE WITH AMINES
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The photochemistry of pyridine N-oxide (1a) and the corresponding 4-benzyl (1b), 4-phenyl (1c), and 2,6-dimethyl (1d) derivatives has been investigated or reinvestigated.Substrates 1a and 1b yield a small amount of the corresponding 2-acylpyrroles (5a,b) as the only isolable product, 1d yields 5d in moderate yield and 1c yields 5c in aprotic and the 2-pyridone 7c in protic solvents.In the presence of diethylamine isomeric 5-diethylaminopentadienenitriles (3,4) are obtained in moderate yield along with deoxygenated pyridines (6).Under this condition no 5 is formed, but the yield of 7 is unchanged.These reactions are most economically accunted for by admitting that nitrene 11 is formed as an intermediate and undergoes rearrangement to pyrroles 5 or polymerization to tars, or it can be trapped by amines (proton abstraction followed by nucleophilic substitution) to yield products 3 and 4.The lactams 7 arise directly from the N-oxide singlet excited state, which is also involved in the deoxygenation by amines.
- Albini, Angelo,Fasani, Elisa,Lohse, Christian
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p. 113 - 124
(2007/10/02)
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