Recent developments in the chemistry of sydnones and sydnone imines

Cherepanov, I. A.; Moiseev, S. K.

doi:10.1016/bs.aihch.2019.11.003

Cited by 35 publications

(29 citation statements)

References 209 publications

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“…N 3 -Substituted sydnone imines 1 can be synthesized according to a standard method [ 30 , 31 ] via nitrosation of the corresponding amino nitriles 2 followed by cyclization to the target mesoionic heterocycle ( Scheme 2 ). However, the cyclization is reversible and possible ring cleavage occurs through several degradation pathways depending on the solvent and pH of the reaction media.…”

Section: Sydnone Iminesmentioning

confidence: 99%

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Ферштат

Zhilin

2021

Molecules

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Nitric oxide (NO) is a key signaling molecule that acts in various physiological processes such as cellular metabolism, vasodilation and transmission of nerve impulses. A wide number of vascular diseases as well as various immune and neurodegenerative disorders were found to be directly associated with a disruption of NO production in living organisms. These issues justify a constant search of novel NO-donors with improved pharmacokinetic profiles and prolonged action. In a series of known structural classes capable of NO release, heterocyclic NO-donors are of special importance due to their increased hydrolytic stability and low toxicity. It is no wonder that synthetic and biochemical investigations of heterocyclic NO-donors have emerged significantly in recent years. In this review, we summarized recent advances in the synthesis, reactivity and biomedical applications of promising heterocyclic NO-donors (furoxans, sydnone imines, pyridazine dioxides, azasydnones). The synthetic potential of each heterocyclic system along with biochemical mechanisms of action are emphasized.

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Section: Sydnone Iminesmentioning

confidence: 99%

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Ферштат

Zhilin

2021

Molecules

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“…The munchnones 14 are very reactive azomethine ylides which undergo 1,3dipolar cycloaddition with a wide variety of dipolarophiles. 38 The sydnones 15, 39 associated with a azomethine imine, also undergo 1,3-dipolar cycloadditions but the more electronegative ring nitrogen makes them less reactive. This is attributable to the -h term in Equation 4.…”

Section: The Localised Bond Model Of Two-and Three-centre Bondsmentioning

confidence: 99%

The influence of electronegativity on linear and triangular three-centre bonds

Ramsden¹

2020

Arkivoc

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Electronegativity differences between bonding atoms have major effects on the strengths of chemical bonds but they affect two-centre and three-centre bonds in different ways and with different consequences. The effect on two-centre bonds was recognised almost 100 years ago but the influence of electronegativity difference on three-centre bonding has received less attention. Molecular orbital models of three-centre bonding are discussed and their application to the understanding of the properties of three-centre bonded species illustrated.

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“…The 1,3-dipolar cycloadditions reactions [ 1 ], also known as “Huisgen reactions” [ 2 ], involving 1,3-dipoles from the class of N -ylides [ 3 , 4 , 5 , 6 ], mesoionic compounds such as munchnones [ 7 , 8 ] and sydnones [ 9 , 10 ] and many others [ 11 , 12 ], have been intensively studied in obtaining a wide range of five membered heterocycles ( Figure 1 ) [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-(2-Fluorophenyl)pyrazoles by 1,3-Dipolar Cycloaddition of the Corresponding Sydnones

et al. 2021

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3-Arylsydnones bearing fluorine and bromine atoms on the benzene ring were synthesized from N-nitroso-2-fluorophenylglycines and characterized by NMR spectroscopy. These were employed further in synthesis of the corresponding 1-(2-fluorophenyl)pyrazoles by 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate (DMAD) as activated dipolarophile. The sydnones as reaction intermediates were characterized by single crystal X-ray diffraction analysis showing interesting features such as halogen bonding as an important interaction in modeling the crystal structure.

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Recent developments in the chemistry of sydnones and sydnone imines

Cited by 35 publications

References 209 publications

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

The influence of electronegativity on linear and triangular three-centre bonds

Synthesis of 1-(2-Fluorophenyl)pyrazoles by 1,3-Dipolar Cycloaddition of the Corresponding Sydnones

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