- Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
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Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.
- Zheng, Yuanqin,Zhou, Yuqiao,Zhang, Yan,Deng, Pengchi,Zhao, Xiaohu,Jiang, Shichao,Du, Guangxi,Shen, Xin,Xie, Xinyu,Su, Zhishan,Yu, Zhipeng
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- 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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- 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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- Ultrafast Click Chemistry with Fluorosydnones
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We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone PdIIprecursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 104m?1s?1, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [18F]Selectfluor.
- Liu, Hui,Audisio, Davide,Plougastel, Lucie,Decuypere, Elodie,Buisson, David-Alexandre,Koniev, Oleksandr,Kolodych, Sergii,Wagner, Alain,Elhabiri, Mourad,Krzyczmonik, Anna,Forsback, Sarita,Solin, Olof,Gouverneur, Véronique,Taran, Frédéric
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p. 12073 - 12077
(2016/11/16)
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- Synthesis, anti-bacterial, and anti-fungal activity of sydnone-based aromatic compounds
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In order to investigate the biological importance of sydnone ring system, two new series viz. 4-(N-(4-(3-(substitutedphenyl)acryloyl) phenyl) sulfamoyl)-3-p-tolyl-sydnone (Series-A) and 4-(N-(4-(5-(substitutedphenyl)isoxazol-3-yl)phenyl)4-sulfamoyl)-3-p-t
- Akbari, Vikunjana K.,Chothani,Patel, Yogesh M.,Patel, Keshav C.
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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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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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- 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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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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p. 8840 - 8851
(2012/01/02)
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- Synthesis, antibacterial and analgesic activities of 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(4-methylphenyl) sydnones
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A series of sydnone derivatives containing styryl ketone moiety, 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(4-methylphenyl)sydnones (6a-i) has been synthesized and characterized by spectral data. The synthesized compounds have been screened for prelimin
- Deshpande, Shreenivas R.,Vasantakumar Pai
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experimental part
p. 59 - 64
(2011/01/03)
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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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- 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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- One-pot conversion of N-arylglycines to sydnones efficiently promoted by bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex Cl2-dabco in the presence of NaNO2/Ac2O under neutral condition
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Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl2-DABCO), has been found as an active chlorine complex for effective one-pot conversion of various N-arylglycines to sydnones in high yields (85-95%) under mild and neutral condition.
- Azarifar, Davood,Ghasemnejad-Bosra, Hassan,Tajbaksh, Mahmood,Habibzadeh, Setareh
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p. 1815 - 1819
(2008/03/14)
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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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- N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an efficient promoter for one-pot conversion of N-arylglycines to sydnones in the presence of NaNO2/Ac2O under neutral conditions
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N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization
- Azarifar, Davood,Ghasemnejad-Bosra, Hassan,Ghorbani-Vaghei, Ramin,Tajbaksh, Mahmood
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p. 2343 - 2347
(2007/10/03)
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- Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions: Subsequent bromination of these sydnones to their
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1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac 2O in high yields (80-
- Azarifar, Davood,Ghasemnejad-Bosra, Hassan
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p. 1123 - 1126
(2007/10/03)
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