- Mechanosynthesis of sydnone-containing coordination complexes
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N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.
- Pétry, Nicolas,Vanderbeeken, Thibaut,Malher, Astrid,Bringer, Yoan,Retailleau, Pascal,Bantreil, Xavier,Lamaty, Frédéric
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p. 9495 - 9498
(2019/08/15)
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- Synthesis and crystal structure of 4-trifluoroacetyl-3-phenylsydnone
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4-Trifluoroacetyl-3-phenylsydnone was first synthesized by trifluoromethylation of 4-formyl-3-phenylsydnone followed by oxidation of the corresponding trifluoromethyl alcohol. The structure of the product was determined by single-crystal X-ray analysis.
- Kawase, Masami,Saijo, Ryosuke,Mori, Shigeki,Uno, Hidemitsu
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p. 2103 - 2110
(2017/11/21)
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- Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions
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A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including high-resolution mass measurements and X-ray diffraction data.
- Dürüst, Ya?ar,Y?ld?z, Elif,Karaku?, Hamza,Kariuki, Benson M.
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p. 660 - 670
(2017/03/24)
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- 1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)
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1,3-Dipolar cycloaddition reaction of sydnone-N-ylides, as model bis(1,3-dipoles), with acetylenic dipolarophiles in 1,2-epoxybutane under reflux gave exclusively pyrroloazines containing a sydnone moiety that resulted by preferred reaction of the N-ylide
- Albota, Florin,Dr?ghici, Constantin,Caira, Mino R.,Dumitrascu, Florea
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p. 9095 - 9100
(2015/11/09)
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- 4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne
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New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.
- Plougastel, Lucie,Koniev, Oleksandr,Specklin, Simon,Decuypere, Elodie,Créminon, Christophe,Buisson, David-Alexandre,Wagner, Alain,Kolodych, Sergii,Taran, Frédéric
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supporting information
p. 9376 - 9378
(2014/08/05)
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- One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction
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A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.
- Specklin, Simon,Decuypere, Elodie,Plougastel, Lucie,Aliani, Soifia,Taran, Frédéric
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p. 7772 - 7777
(2014/10/15)
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- Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening
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An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents. Copyright
- Kolodych, Sergii,Rasolofonjatovo, Evelia,Chaumontet, Manon,Nevers, Marie-Claire,Creminon, Christophe,Taran, Frederic
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supporting information
p. 12056 - 12060
(2013/12/04)
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- Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone
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A novel series of 1-substituted aminomethyl-3-[1-(4-isobutylphenyl)ethyl]- 4-(3-aryl-4-sydnonylidene) amino-1,2,4-triazol-5-thiones (9), was prepared from the 3-[1-(4-isobutylphenyl)ethyl]-4-(3-aryl-4-sydnonylidene) amino 5-mercapto-1,2,4-triazoles (8) by aminomethylation with formaldehyde and secondary amine. The structures of Schiff bases (8) and Mannich bases (9) were characterized on the basis of IR, NMR, mass spectra1 data and elemental analysis. The newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Mannich bases (9) carrying piperidine and morpholine residues showed promising anti-inflammatory and analgesic activity.
- Nithinchandra,Kalluraya,Aamir,Shabaraya
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experimental part
p. 597 - 604
(2012/09/11)
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- Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes
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A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl
- Fang, Yuesi,Wu, Chunrui,Larock, Richard C.,Shi, Feng
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experimental part
p. 8840 - 8851
(2012/01/02)
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- Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones
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A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.
- Wu, Chunrui,Fang, Yuesi,Larock, Richard C.,Shi, Feng
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supporting information; experimental part
p. 2234 - 2237
(2010/08/04)
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- Cross coupling of bromo sydnones: Development of a flexible route toward functionalized pyrazoles
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(Chemical Equation Presented) The application of a Suzuki cross coupling approach to a range of C-4 substituted sydnones from a 4-bromosydnone is described. Moreover, the potential of this approach to prepare a diverse range of pyrazoles is demonstrated.
- Browne, Duncan L.,Taylor, John B.,Plant, Andrew,Harrity, Joseph P. A.
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supporting information; experimental part
p. 396 - 400
(2009/04/07)
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- Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation
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Novel 1-aryl-3-(5-nitro-2-thienyl)-4-aroyl-pyrazoles 7 have been synthesized by the 1,3-dipolar cycloaddition of 3-arylsydnones 3 with 1-aryl-3-(5-nitro-2-thienyl)-2-propyn-1-ones 6. The newly synthesized compounds were well characterized by elemental analysis, IR, 1H NMR and mass spectral studies. They were also screened for their antibacterial and antifungal activities against a variety of microorganisms and the results of such studies have been discussed in this article.
- Satheesha Rai,Kalluraya, Balakrishna,Lingappa,Shenoy, Shaliny,Puranic, Vedavati G.
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p. 1715 - 1720
(2008/12/20)
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- Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers
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A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.
- Mallur, Shanta G.,Tiwari,Raju, B. China,Babu, K. Suresh,Ali, A. Zehra,Sastry,Rao, J. Madhusudana
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p. 1686 - 1689
(2008/09/19)
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- Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis
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Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.
- Azarifar, Davood,Bosra, Hassan Ghasemnejad,Zolfigol, Mohammad-Ali,Tajbaksh, Mahmood
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p. 175 - 181
(2007/10/03)
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- Structural effects on the n-nitrosation of amino acids
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The relative importance of three different routes for the N-nitrosation of amino acids (nitrosation by N2O3, by NO+/NO2H2+ and by intramolecular migration of the nitroso group from the init
- Gil, Rafael,Casado, Julio,Izquierdo, Carmen
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p. 495 - 504
(2007/10/03)
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- Synthesis and reactions of 9,10-diazatetracyclo-[6.3.0.0.4,110.5.9]undecanes
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The tandem 1,3-dipolar cycloaddition between sydnones and 1,5-cyclooctadiene provides 9,10-diazatetracyclo[6.3.0.0.4,110.5,9]undecanes (the Weintraub reaction) in modest to good yields.
- Gribble, Gordon W.,Hirth, Bradford H.
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p. 719 - 726
(2007/10/03)
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- Synthesis and antiinflammatory, analgesic, and antipyretic testing of 4- [1-oxo-(3-substituted aryl)-2-propenyl]-3-phenylsydnones and of 3-[4-[3- (substituted aryl)-1-oxo-2-propenyl]phenyl]sydnones
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Two series of styrylcarbonyl 3-phenylsydnone derivatives, 4-[1-oxo-(3- substituted aryl)-2-propenyl]-3-phenylsydnones (series I, 1-21) and 3-[4-[3- (substituted aryl)-1-oxo-2-propenyl]phenyl]sydnones (series II, 22-40), were synthesized and evaluated pharmacologically at a dose of 100 mg/kg po. Eleven compounds in series I plus one in series II and six in series I plus seven in series II were active in the carrageenan-induced edema and acetic acid- induced writhing assays, respectively. Compound 35 in the latter assay showed activity somewhat similar to that of the positive control drug, aspirin, administered at the same dosage. Compounds 11, 17, and 23 showed activity in both assays, and 23 also was active in the adjuvant-induced arthritis assay.
- Satyanarayana,Rao
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p. 263 - 266
(2007/10/02)
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- The Efficient Synthesis of 3-Arylsydnones Under Neutral Conditions
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Various substituted aryl sydnones can be prepared in high yield under mild, neutral conditions by nitrosation of the appropriate aryl glycine with isoamyl nitrite in dimethoxyethane followed by cyclization with trifluoroacetic anhydride.
- Applegate, Jacqueline,Turnbull, Kenneth
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p. 1011 - 1012
(2007/10/02)
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- Photochemistry of N-nitroso-N-alkyl amino acids: a facile oxidative decarboxylation
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Several N-alkyl or N-phenyl-N-nitroso α-amino acids were synthesized and were shown to photolytically rearrange to amidoximes with concurrent decarboxylation in solution or solid states without the presence of externally added acids.In contrast, N-nitrosonipecotinic acid, a N-nitroso β-amino acid, as well as N-nitrosopiperidine in the presence of acetic acid were not photolabile.The photolability of N-nitroso α-amino acids was ascribed to the presence of an intramolecular association between the nitrosamino and carboxyl groups through hydrogen bonding.The species having the hydrogen bonding through the nitroso oxygen in the Z-configuration was believed to be photolabile and decomposed to alkylideneimines as the primary product.The mechanism of the oxidative photorearrangement was discussed.
- Chow, Yuan L.,Horning, Douglas P.,Polo, Joel
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p. 2477 - 2483
(2007/10/02)
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