Trasformazioni eterocicliche di 1,2,4-ossadiazoli fluorurati in reazioni ANRORC-like

Characterization of isomeric organic cations by Esi/MS: 3-alkyl-5-(4-N-methylpyridinium)-1,2,4-oxadiazole cations, 5-alkyl-3-(4-N-methylpyridinium)-1,2,4-oxadiazole cations and 3-perfluoroakyl-5-(4-N-methylpyridinium)-1,2,4-oxadiazole cations, 5-perfluoroakyl-3-(4-N-methylpyridinium)-1,2,4-oxadiazole cations

Anrorc rearrangements of fluorinated 1,2,4-oxadiazoles as an expedient route to fluorinated heterocycles

Composti eterociclici fluorurati. Un approccio fotochimico alla sintesi di chinazolin-4-oni

Designing fluorous domains. Pyridinium salts bearing a perfluoroalkylated oxadiazole moiety

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Recent Advances in 1,2,4-Oxadiazole Chemistry

Fluorinated heterocyclic compounds from ring-to-ring transformations of O-N bond containing azoles

Sintesi one-pot di N-ossidi di 2-ammino-pirimidine fluorurate. Riarrangiamenti competitivi “four-atom side-chain” di 1,2,4-ossadiazoli

Nuovi Riarrangiamenti Boulton-Katritzky di derivati 1,2,4-ossadiazolici contenenti un atomo di carbonio nucleofilo in catena laterale

Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. A Cascade Isoxazole-1,2,4-Oxadiazole-Oxazole Rearrangement

The thermal rearrangements of 3-acylamino-5-methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 1 showed that the Boulton-Katritzky (BK) rearrangement, producing the less stable 3-acetonyl- 1,2,4-oxadiazoles 5, is a much more favored process than either the migration-nucleophilic attack-cyclization (MNAC) or the ring contraction-ring expansion (RCRE). In turn, an increase in reaction temperature will promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazo…

Studio dell’effetto dei sostituenti sul riarrangiamento fotoindotto di diaril-1,2,4-ossadiazoli in zeolite NaY

Synthesis of trifluoromethylated 2-benzoyl- and 3-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivative

Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated b-dicarbonyl compounds and subsequent base-induced BoultoneKatritzky Rearrangement (BKR) of the isolated b-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.

Synthesis, Reactivity, Biological Activity and Applications of Fluorinated Oxadiazoles and Thiadiazoles

A literature survey of the chemistry of fluorinated oxadiazoles and thiadiazoles is presented. The core part on synthetic procedures is given by type of heterocycle and includes recent developments up to the end of 2012. Reactivity is discussed when induced by the presence of the fluorinated moiety. Selected examples of bioactive compounds and applications are illustrated.

Sintesi di ossadiazoli fluorurati come nuovi Low molecular weight hydrogelators

Microreattori fluorurati. Studio della reazione "ene" con ossigeno singoletto in zeolite NAY modificata con cationi fluoroorganici

Fluoroarylation of hydroxylated molecules with 5-pentafluorophenyl-1,2,4-oxadiazoles

Experimental and DFT studies on competitive heterocyclic rearrangements. part 2: A one-atom side-chain versus the classic three-atom side-chain (Boulton-Katritzky) ring rearrangement of 3-acylamino-1,2,4-oxadiazoles

The experimental investigation of the base-catalyzed rearrangements of 3-acylamino-1,2,4-oxadiazoles evidenced a new reaction pathway which competes with the well-known ring-degenerate Boulton- Katritzky rearrangement (BKR). The new reaction consists of a one-atom side-chain rearrangement that is base-activated, occurs at a higher temperature than the BKR, and irreversibly leads to the corresponding 2-acylamino-1,3,4-oxadiazoles. An extensive DFT study is reported to elucidate the proposed reaction mechanism and to compare the three possible inherent routes: (i) the reversible three-atom side-chain ring-degenerate BKR, (ii) the ring contraction-ring expansion route (RCRE), and (iii) the one…

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Fotochimica organica in zeolite: dalle fotoossidazioni ai riarrangiamenti eterociclici

Applications of ring rearrangements involving a participating side chain for the synthesis of five-membered heterocycles

Fluorinated heterocycles from 1,2,4-oxadiazole precursors. Synthesis of 3-amino-indazoles

Novel ANRORC rearrangements of 1,2,4-oxadiazoles