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 31 publications

(29 citation statements)

References 209 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

View full text Add to dashboard Cite

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.

show abstract

Section: Sydnone Iminesmentioning

confidence: 99%

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

Ферштат

Zhilin

2021

Molecules

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

Recent developments in the chemistry of sydnones and sydnone imines

Cited by 31 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

Contact Info

Product

Resources

About