Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Lücke, Ana-Luiza; Pruschinski, Lucas; Freese, Tyll; Schmidt, Andreas

doi:10.24820/ark.5550190.p011.231

Cited by 7 publications

(2 citation statements)

References 45 publications

(61 reference statements)

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“…Using a combination of molecular docking and molecular dynamics simulations a series of iminosydnone-based insecticides was designed and synthesized [ 65 ]. Aside from biomedical applications, sydnone imine derivatives were used as additives or catalysts in Pd-catalyzed cross-coupling reactions [ 66 , 67 ]. Additionally, recently, the first representatives of sydnone imine-based dense energetic materials with high detonation performance were prepared [ 68 ].…”

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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“…Besides, a sydnone imine such as molsidomine was used to prepare selenium adducts as well as gold and palladium complexes . Thereafter, all complexes have been studied in Suzuki–Miyaura, Sonogashira–Hagihara, and Buchwald–Hartwig couplings . An alternative approach in the preparation of the anionic compound is from 4-bromosydnone by exchanging its bromine toward lithium on treatment with BuLi .…”

Section: Introductionmentioning

confidence: 99%

Anionic N-Heterocyclic Carbene Gold(I) Complexes from Sydnones as a Precarbenic Unit: A Comprehensive Study of the Au–C sp² Bond Stability Compared to Its “Relative” Imidazole

Vita,

Schiel,

Lo Fiego

et al. 2023

Organometallics

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A series of sydnones was used as N-heterocyclic carbene (NHC) precursors to synthesize gold(I) complexes by a two-step reaction. The first reaction step involves the deprotonation of the sydnone to obtain the corresponding anionic NHC. Second, the metal precursor was added to afford the corresponding gold(I) complex. At this point, the complex obtained depends on the nature of the metal precursor. The use of AuCl(tht) allows one to obtain the monocarbene complex (sydnone−Au−tht), and by contrast, the use of a gold(I) imidazole complex allows one to obtain the bis-carbene complex (syndone−Au−imidazole). Furthermore, the use of sydnone as a metal precursor (sydnone−Au−tht) yields the formation of asymmetric bis-sydnones complexes (sydnone−Au−sydnone'). All gold(I) complexes have been characterized by NMR, Fourier transform infrared spectroscopy (FT-IR), ultraviolet−visible (UV−vis), and elemental analyses. Density functional theory (DFT) methods were used in order to theoretically establish a structure/stability relationship and describe the catalytic effect of these complexes and their imidazole analogues.

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Mesomeric Betaines Based on Adamantylated 1,2,4‐Triazolo[4,3‐a]pyrimidin‐5‐ones: Synthesis, Structure and Conversion into Anionic N‐Heterocyclic Carbenes

Sheina

Шестакова

Деев

et al. 2023

Chemistry An Asian Journal

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The CÀ N coupling of 1,2,4-triazolo[1,5-a]pyrimidin-7-ones with 1-adamantanol/1-bromoadamantane leads to 1,2,4-triazolo[4,3-a]pyrimidinium-5-olates, which are represented as mesomeric betaines (MBs). The formation of MBs involves not only N-alkylation of heterocyclic framework but also the rearrangement leading to a change in the type of fusion between pyrimidine and 1,2,4-triazole fragments. The structures of the obtained products were confirmed by the Xray analysis and measurements of 13 CÀ 13 C (J CC ) coupling constants in the 1D 13 C NMR spectra of selectively 13 C-labeled samples. Treatment of the betaines with lithium bis(trimethylsilyl)amide (LiHMDS) gave anionic carbenes, which were detected by 13 C NMR spectroscopy and were trapped by reactions with phenyl isothiocyanate and sulfur. Density functional theory (DFT) and the quantum theory of atoms in molecules (QTAIM) analyses allowed for an insight into the electronic structure of the obtained betaines and N-heterocyclic carbene derivatives.[a] E.

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Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Cited by 7 publications

References 45 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

Anionic N-Heterocyclic Carbene Gold(I) Complexes from Sydnones as a Precarbenic Unit: A Comprehensive Study of the Au–C sp² Bond Stability Compared to Its “Relative” Imidazole

Mesomeric Betaines Based on Adamantylated 1,2,4‐Triazolo[4,3‐a]pyrimidin‐5‐ones: Synthesis, Structure and Conversion into Anionic N‐Heterocyclic Carbenes

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Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Cited by 7 publications

References 45 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

Anionic N-Heterocyclic Carbene Gold(I) Complexes from Sydnones as a Precarbenic Unit: A Comprehensive Study of the Au–C sp2 Bond Stability Compared to Its “Relative” Imidazole

Mesomeric Betaines Based on Adamantylated 1,2,4‐Triazolo[4,3‐a]pyrimidin‐5‐ones: Synthesis, Structure and Conversion into Anionic N‐Heterocyclic Carbenes

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Anionic N-Heterocyclic Carbene Gold(I) Complexes from Sydnones as a Precarbenic Unit: A Comprehensive Study of the Au–C sp² Bond Stability Compared to Its “Relative” Imidazole