- 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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- Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines
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A small library of diarylsydnones (DASyds) was constructed based on aryl-pairing combinations and subjected to click reaction toward alkenes under photoirradiation with high efficiency. We were able to demonstrate the utility of DASyds for highly fluorescent turn-on ligation targeting the trans-cyclooct-4-en-1-ol moieties on protein.
- Zhang, Linmeng,Zhang, Xiaocui,Yao, Zhuojun,Jiang, Shichao,Deng, Jiajie,Li, Bo,Yu, Zhipeng
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p. 7390 - 7394
(2018/06/13)
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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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- 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 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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- Reactions of 4-acetylsydnones with hydrazine: Formation of 2,4- dihydropyrol-3-ones
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Reactions of 4-acetylsydnones with hydrazine at room temperature yielded a series of 2,4-dihydropyrazol-3-ones. The cycloaddition via sydnone rings with loss of a nitrogen oxide ion is a new type of reaction for the application of sydnone in organic synth
- Tien, Hsien-Ju,Lin, Shaw-Tao,Yang, Mei-Lin
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