Fluorine-containing 1,10-phenanthrolines synthesis: an original and efficient approach by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various nucleophiles

Shibata, Dai; Okada, Etsuji; Miyaoku, Takayuki; Molette, Jérôme; Médebielle, Maurice

doi:10.1016/j.tet.2009.05.047

Cited by 2 publications

(3 citation statements)

References 37 publications

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“…Scheme 13. Povarov Reaction Developed by Shibata et al 255,256 Liu et al 303,304 developed platinum(II) complexes based on fluorenyl-derived phen (Scheme 31) in order to increase the πdonating ability of the aryl ring to improve the non-linear absorption properties of the corresponding complexes.…”

Section: Friedlandler Reactionmentioning

confidence: 99%

“…For example, Sharghi et al 254 have synthesized the substituted phen 131 by reacting O-propargylated salicylaldehyde with 8-aminoquinoline catalyzed by a copper(II) complex (Cu(II)BHPPDAH, where BHPPDAH = N,N-bis(2hydroxyphenyl)pyridine-2,6-dicarboxamide) in PEG at 100 °C (Scheme 12). Shibata et al 255,256 have reported the synthesis of Npropargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine 132 that can react with various amines to form fluorine-containing phen (Scheme 13) with good yields (Table 11). In this case the reaction has been adapted, probably to avoid the use of highly explosive propargylaldehyde.…”

Section: Alkynes As One Of the Componentsmentioning

confidence: 99%

“…Shibata et al , have reported the synthesis of N -propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine 132 that can react with various amines to form fluorine-containing phen (Scheme ) with good yields (Table ). In this case the reaction has been adapted, probably to avoid the use of highly explosive propargylaldehyde.…”

Section: Convergent Synthetic Pathwaysmentioning

confidence: 99%

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Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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1,10-Phenanthroline (phen) is one of the most popular ligands ever used in coordination chemistry due to its strong affinity for a wide range of metals with various oxidation states. Its polyaromatic structure provides robustness and rigidity, leading to intriguing features in numerous fields (luminescent coordination scaffolds, catalysis, supramolecular chemistry, sensors, theranostics, etc.). Importantly, phen offers eight distinct positions for functional groups to be attached, showcasing remarkable versatility for such a simple ligand. As a result, phen has become a landmark molecule for coordination chemists, serving as a must-use ligand and a versatile platform for designing polyfunctional arrays. The extensive use of substituted phenanthroline ligands with different metal ions has resulted in a diverse array of complexes tailored for numerous applications. For instance, these complexes have been utilized as sensitizers in dye-sensitized solar cells, as luminescent probes modified with antibodies for biomaterials, and in the creation of elegant supramolecular architectures like rotaxanes and catenanes, exemplified by Sauvage’s Nobel Prize-winning work in 2016. In summary, phen has found applications in almost every facet of chemistry. An intriguing aspect of phen is the specific reactivity of each pair of carbon atoms ([2,9], [3,8], [4,7], and [5,6]), enabling the functionalization of each pair with different groups and leading to polyfunctional arrays. Furthermore, it is possible to differentiate each position in these pairs, resulting in non-symmetrical systems with tremendous versatility. In this Review, the authors aim to compile and categorize existing synthetic strategies for the stepwise polyfunctionalization of phen in various positions. This comprehensive toolbox will aid coordination chemists in designing virtually any polyfunctional ligand. The survey will encompass seminal work from the 1950s to the present day. The scope of the Review will be limited to 1,10-phenanthroline, excluding ligands with more intracyclic heteroatoms or fused aromatic cycles. Overall, the primary goal of this Review is to highlight both old and recent synthetic strategies that find applicability in the mentioned applications. By doing so, the authors hope to establish a first reference for phenanthroline synthesis, covering all possible positions on the backbone, and hope to inspire all concerned chemists to devise new strategies that have not yet been explored.

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Section: Friedlandler Reactionmentioning

confidence: 99%

Section: Alkynes As One Of the Componentsmentioning

confidence: 99%

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Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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ChemInform Abstract: Fluorine‐Containing 1,10‐Phenanthrolines Synthesis: An Original and Efficient Approach by the Pyridine‐Ring Formation Reaction of N‐Propargyl‐5,7‐bis‐(trifluoroacetyl)‐8‐quinolylamine with Various Nucleophiles.

et al. 2009

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Fused pyridine derivatives R 0450Fluorine-Containing 1,10-Phenanthrolines Synthesis: An Original and Efficient Approach by the Pyridine-Ring Formation Reaction of N-Propargyl-5,7-bis-(trifluoroacetyl)-8-quinolylamine with Various Nucleophiles. -Cyclization of title N-propargylquinolylamine (I) with various thiols, phenols and amines provides access towards a diversity of 3-substituted 1,10-phenanthrolines (III), (V), (VII) and (X). The isolation of the reactive dihydrophenanthrolinol derivative [cf. (IX)] is achieved only in the reaction of secondary amines (VIII). -(SHIBATA, D.; OKADA, E.; MIYAOKU, T.; MOLETTE, J.; MEDEBIELLE, M.; Tetrahedron 65 (2009) 31, 6189-6195; Dep. Chem. Sci. Eng., Fac. Eng., Kobe Univ., Nada, Kobe 657, Japan; Eng.) -Mischke 47-121

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Fluorine-containing 1,10-phenanthrolines synthesis: an original and efficient approach by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various nucleophiles

Cited by 2 publications

References 37 publications

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

ChemInform Abstract: Fluorine‐Containing 1,10‐Phenanthrolines Synthesis: An Original and Efficient Approach by the Pyridine‐Ring Formation Reaction of N‐Propargyl‐5,7‐bis‐(trifluoroacetyl)‐8‐quinolylamine with Various Nucleophiles.

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