cas 3356-89-6, 5-chloro-3-phenyl-oxazole | Articles data

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1-(2: H -Azirine-2-carbonyl)benzotriazoles: Building blocks for the synthesis of pyrrole-containing heterocycles
A one-pot method was developed for the preparation of 2H-azirine-2-carbonylbenzotriazoles, formed by the reaction of benzotriazole with 2H-azirine-2-carbonyl chlorides, which were generated by the Fe(ii)-catalyzed isomerization of 5-chloroisoxazoles. The Co(ii)-catalyzed reaction of 2H-azirine-2-carbonylbenzotriazoles with 1,3-diketones provides 2-((benzotriazol-1-yl)carbonyl)pyrroles in moderate to good yields. Base-promoted annulations of 2-((benzotriazol-1-yl)carbonyl)pyrroles with aldehydes, ketones, isocyanates and isothiocyanates afford various substituted pyrrolo[1,2-c]oxazole and 1H-pyrrolo[1,2-c]imidazole derivatives in moderate to high yields. The 6-acyl group of these adducts can be removed by triflic acid, giving further new pyrrolo-fused O- and N-heterocycles, such as 6-unsubstituted pyrrolo[1,2-c]oxazol-1(3H)-one and 1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione, while the 6-acetyl substituent of 1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione, when treated with POCl3/pyridine, is transformed into the 6-ethynyl substituent.
Bodunov, Vladimir A.,Galenko, Ekaterina E.,Khlebnikov, Alexander F.,Novikov, Mikhail S.,Shakirova, Firuza M.
p. 2283 - 2296
(2020/04/07)

Synthesis of 5-Chloroisoxazoles Derived from 2,2-Dichlorovinyl Ketones
Abstract: The reactions of 2,2-dichlorovinyl ketones with hydroxylamine hydrochloride give the corresponding oximes. The subsequent heterocyclization of the latter under the action of t-BuOK in t-BuOH results in selective formation of 5-chloro-3-alkyl- or
Popov,Kobelevskaya,Titov,Larina,Rozentsveig
p. 1958 - 1962
(2021/01/13)

General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies
A general platform for the conversion of isoxazol-5-ones to 3,5-disubstituted isoxazoles has been developed via a two-step strategy. The first step leads to the formation of 5-(pseudo)halogenated isoxazoles, while in the second, a variety of heteroalkyl-, heteroaryl-, alkyl-, alkenyl-, alkynyl- and aryl-chains can be installed via nucleophilic substitutions or palladium catalyzed cross-coupling reactions.
Fernandes, Alessandra A. G.,da Silva, Amanda F.,Okada, Celso Y.,Suzukawa, Vitor,Cormanich, Rodrigo A.,Jurberg, Igor D.
p. 3022 - 3034
(2019/05/17)

Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes
Nitrosylsulfuric acid is shown to be a usable reagent for the synthesis of 5-chloroisoxazoles from readily available 1,1-di-chlorocyclopropanes via nitrosation–heterocyclization reaction. A cytotoxicity of some of the prepared 5-chloroisoxazoles towards M
Bondarenko, Oksana B.,Garaev, Zaur M.,Komarov, Arseniy I.,Kuznetsova, Lyubov I.,Gutorova, Svetlana V.,Skvortsov, Dmitry A.,Zyk, Nikolai V.
p. 419 - 420
(2019/08/20)

New azole antagonists with high affinity for the P2Y1 receptor
Five-membered-ring heterocyclic urea mimics have been found to be potent and selective antagonists of the P2Y1 receptor. SAR of the various heterocyclic replacements is presented, as well as side-chain SAR of the more potent thiadiazole ring sy
Ruel, Réjean,L'Heureux, Alexandre,Thibeault, Carl,Daris, Jean-Paul,Martel, Alain,Price, Laura A.,Wu, Qimin,Hua, Ji,Wexler, Ruth R.,Rehfuss, Robert,Lam, Patrick Y.S.
p. 3519 - 3522
(2013/07/05)

Transformations of gem-dichloroarylcyclopropanes in the reaction with NOCl·2SO3. Synthesis of 3-aryl-5-chloroisoxazoles
Nitrosation with complex NOCl·2SO3 of gem-dichloroarylcyclopropanes containing acceptor substituents in the aromatic ring proceeded chemo- and regioselectively affording 3-aryl-5-chloroisoxazoles in high yields. The presence of donor substituents complicated the reaction by the occurrence of competing processes.
Bondarenko,Gavrilova,Murodov,Zefirov,Zyk
p. 186 - 194
(2013/07/25)

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies
The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes 9a-9c were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole derived oxetanes show type T photochromism.
Griesbeck, Axel G.,Franke, Marco,Neudoerfl, Joerg,Kotaka, Hidehiro
experimental part
p. 127 - 134
(2011/05/16)

Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)
The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50s of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min.
Nantermet, Philippe G,Barrow, James C.,Lundell, George F.,Pellicore, Janetta M.,Rittle, Kenneth E.,Young, MaryBeth,Freidinger, Roger M.,Connolly, Thomas M.,Condra, Cindra,Karczewski, Jerzy,Bednar, Rodney A.,Gaul, Stanley L.,Gould, Robert J.,Prendergast, Kris,Selnick, Harold G.
p. 319 - 323
(2007/10/03)

Reaction of halogenated cyclopropanes and nitrosyl cation: Preparation of isoxazoles
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Lin,Kuo,Yang
p. 5229 - 5231
(2007/10/03)

SYNTHESIS AND NUCLEOPHILIC SUBSTITUTIONS OF 3-ALKYL-5-CHLOROISOXAZOLES
A 3-alkyl-5-chloroisoxazole synthesis is described based on the cycloaddition of nitrile oxides to 1,1-dichloroethylene, an inexpensive dipolarophile.Substitution of the chloride in these adducts by various nucleophiles is also described.
Stevens, R. V.,Albizati, K. F.
p. 4587 - 4590
(2007/10/02)