18735-78-9Relevant academic research and scientific papers
Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage
Li, Ziyuan,Ma, Ling,Xu, Jinyi,Kong, Lingyi,Wu, Xiaoming,Yao, Hequan
, p. 3763 - 3765 (2012/06/15)
The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C-H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance. The Royal Society of Chemistry 2012.
Solution versus fluorous versus solid-phase synthesis of 2,5-disubstituted 1,3-azoles. Preliminary antibacterial activity studies
Sanz-Cervera, Juan F.,Blasco, Rauel,Piera, Julio,Cynamon, Michael,Ibanez, Ignacio,Murguia, Marcelo,Fustero, Santos
experimental part, p. 8988 - 8996 (2010/03/24)
(Chemical Equation Presented) A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.
Inhibitors of P2X3
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Page/Page column 15, (2008/06/13)
Compounds of formula 1 are modulators of P2X3 useful for the treatment of pain and genito-urinary, gastrointestinal, and respiratory disorders: wherein R1 is —C(═S)CH3, pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, furyl, furylcarbonyl, acetyl, or carbamoyl; R2a and R2b are independently H, methyl, or ethyl; R3 is H or methyl; Y is a bond, —(CR4R5)n— or —CR4═CR5—; wherein R4 and R5 are each independently H or methyl and n is 1 or 2; X is N or CH; A is phenyl, 5-membered heterocyclyl, or 6-membered heterocyclyl; R6, R7 and R8 are each independently H, halo, lower alkyl, cycloalkyl, alkylthio, alkylthio-lower alkyl, alkylsulfonyl-lower alkyl, di(lower alkyl)amino-lower alkyl, morpholinyl-lower alkyl, 4-methyl-piperazinyl-methyl, trifluoromethyl, pyridyl, tetrazolyl, thiophenyl, phenyl, biphenyl, or benzyl (where thiophenyl, phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoromethyl, lower alkoxy or lower alkylthio) or R6 and R7 together form a 5-membered or 6-membered carbocyclic or heterocyclic ring substituted with 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, oxo, halo, thiophenyl-lower alkyl, phenyl, benzyl (where phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoro-methyl, lower alkoxy, lower alkylthio, amino-lower alkyl, lower alkylamino-lower alkyl, or di(lower alkyl)amino-lower alkyl); and pharmaceutically acceptable salts thereof; wherein when R1 is pyrimidin-2-yl, X is N, Y is a bond and A is oxazol-5-yl the carbon atom at position 4 in said oxazol-5-yl is not substituted by propyl when the carbon atom at position 2 in said oxazol-5-yl is substituted by substituted phenyl and the carbon atom at position 4 in said oxazol-5-yl is not substituted by phenyl when the carbon atom at position 2 is substituted by unsubstituted or substituted phenyl.
Solid-phase synthesis of oxazolones and other heterocycles via Wang resin-bound diazocarbonyls
Yamashita, Makoto,Lee, Sang-Hyeup,Koch, Guido,Zimmermann, Juerg,Clapham, Bruce,Janda, Kim D.
, p. 5495 - 5498 (2007/10/03)
The preparation of Wang resin bound α-diazo-β-ketoesters is described. These highly useful intermediates were used for the synthesis of a series of heterocycle libraries, which were obtained from the resin using TFA cleavage. In addition, a novel route for the synthesis of oxazolones using an N-H insertion strategy is disclosed.
Ethyl 2-chlorooxazole-4-carboxylate: A versatile intermediate for the synthesis of substituted oxazoles
Hodgetts, Kevin J.,Kershaw, Mark T.
, p. 2905 - 2907 (2007/10/03)
(formula presented) R1 = Ar, Het, alkenyl R2 = H, Ar, Het, alkenyl, alkynyl R3 = H, CO2H, Ar, Het, alkenyl, alkynyl By using a sequence of regiocontrolled halogenation and palladium-catalyzed coupling reactions,
Synthesis and scintillating efficiencies of 4-functionalised-2,5-Diphenyloxazoles
Clapham, Bruce,Richards, Amanda J.,Wood, Michael L.,Sutherland, Andrew J.
, p. 9061 - 9064 (2007/10/03)
A series of 4-functionalised-2,5-diphenyloxazoles has been synthesised. Each member of the series has been assessed for the ability to scintillate in the presence of ionising radiation. The scintillation counting efficiency of each member of the series has been determined relative to 2,5-diphenyloxazole, a widely used scintillant molecule.
