Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Gómez, Jorge Enrique; Klahn, A. Hugo; Fuentealba, Mauricio; Sierra, Diego; Olea‐Azar, Claudio; Medina, M.

doi:10.1016/j.inoche.2015.10.007

Cited by 16 publications

(2 citation statements)

References 27 publications

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“…35 -4.30 (2) are assigned to the hydrogen nuclei of the substituted ring. These results agree with the values reported for several ferrocenyl complexes [37,44,45]. For compound 1, additional signals were observed at δ 2.94 and δ 2.75 (Figure S4 †), and they were attributed to the presence of the -CH2CH2group.…”

Section: Scheme 1 Synthesis Of Compounds 1 Andsupporting

confidence: 91%

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Gallardo¹,

Arancibia²,

Roussel

et al. 2023

J. Chil. Chem. Soc.

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In the search of new organometallic precursors, this contribution describes a convenient synthesis to obtain new ferrocene-based sulfonyl diamine derivatives. The [(η 5 -C5H4SO2NH-CH2-CH2-NH2)Fe(η 5 -C5H5)] (1) and [(η 5 -C5H4SO2NH-C6H4-NH2)Fe(η 5 -C5H5)] (2) compounds were prepared by the reaction between (η 5 -C5H4SO2Cl)Fe(η 5 -C5H5) and the respective diamine precursor: ethylenediamine (1) or p-phenylenediamine (2) in good yields (86% for 1; 70% for 2). Both compounds were characterized by conventional spectroscopic techniques (infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis) and cyclic voltammetry. In addition, the molecular structure of 1 was determined by single-crystal X-ray diffraction.

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Section: Scheme 1 Synthesis Of Compounds 1 Andsupporting

confidence: 91%

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Gallardo¹,

Arancibia²,

Roussel

et al. 2023

J. Chil. Chem. Soc.

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“…40 The current azines were not subjected to XRD analysis, and to the best of knowledge, they are novel. However, XRD studies of ferrocenylazines bearing the 5-nitrofuran and 5-nitrothiophene scaffolds have previously been conducted by Gómez et al 35,41 and confirmed the (E,E) configuration of these aromatic azines. In this configuration, the 1 H chemical shifts (δ) of the azine bridge protons were found to be in the 8.38-8.36 ppm region, wherein those of protons H-6 and H-1′ of the current azines also fell.…”

Section: Chemistrymentioning

confidence: 91%

Design, synthesis, electrochemistry and anti-trypanosomatid hit/lead identification of nitrofuranylazines

Saayman¹,

Kannigadu²,

Aucamp³

et al. 2023

RSC Med. Chem.

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New multifunctional heterobinuclear palladium (II) complexes based on organometallic dithiocarbazate ligands

Huentupil

Chung

Novoa

et al. 2020

Applied Organom Chemis

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In the research of new compounds with multifunctional applications, heterobinuclear palladium (II) complexes based on organometallic dithiocarbazates (DTCZs) have been isolated. The organometallic DTCZ ligands of the general formula [{(η5‐C5H4)‐CH=NNHC(S)SCH3}]MLn [MLn = Re (CO)3 (2a); Mn (CO)3 (2b); FeCp (2c)] were prepared by the reaction between formyl organometallic precursors (1a−c) with S‐methyldithiocarbazate. Subsequently, a two‐step reaction of 2a−c with: (i) K2[PdCl4] and (ii) PPh3 yielded heterobinuclear complexes [Pd{MLn(η5‐C5H4)‐CH=NNHC(S)SCH3}–(Cl)(PPh3)] [MLn = Re (CO)3 (3a); Mn (CO)3 (3b); FeCp (3c)]. All compounds were characterized by conventional spectroscopic techniques (infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis). In addition, the molecular structures of 2a, 2c and 3c were determined by single‐crystal X‐ray diffraction. The new palladium (II) complexes (3a−c) were evaluated as antiproliferative agents against non‐small cell lung cancer cells (H1299 cells). Complexes 3a and 3b containing cyrhetrenyl‐ and cymantrenyl‐DTCZ ligands, respectively, were more active than their ferrocenyl analogue 3c. The activity was associated with the electron‐withdrawing properties of the (η5‐C5H4)M (CO)3 moieties and their better lipophilicity than that of the ferrocenyl analogue. In addition, we studied the capacity of metalloligands (2a−c) and palladium (II) complexes (3a−c) to remove methylene blue in water under UV–visible light irradiation. The results established that the complexes showed moderate efficiency and were less active than their corresponding free ligands.

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Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Cited by 16 publications

References 27 publications

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Rational Design and Convenient Synthesis of Two Novel Ferrocene-Based Sulfonyl Diamine Precursors

Design, synthesis, electrochemistry and anti-trypanosomatid hit/lead identification of nitrofuranylazines

New multifunctional heterobinuclear palladium (II) complexes based on organometallic dithiocarbazate ligands

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