The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases

Patrick W.V. Butler; Jas S. Ward

doi:10.1002/zaac.201900063

The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases

Patrick W.V. Butler, Jas S. Ward^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Whilst pursuing the synthetic utility of quinoline-based tin complexes, Me ₂ Sn(Quin-NO ₂ ) ₂ (1) and Ph ₂ Sn(Quin-NO ₂ ) ₂ (2) (Quin-NO ₂ = 5-nitroquinolino-8-oate) were synthesized bearing coordinatively inert nitro groups. Conventional reduction methodologies successfully converted 1 to Me ₂ Sn(Quin-NH ₂ ) ₂ (3) and 2 to Ph ₂ Sn(Quin-NH ₂ ) ₂ (4) (Quin-NH ₂ = 5-aminoquinolino-8-oate). The synthetically useful amine groups proved difficult to exploit in the presence of the central tin atom, however, a complete Schiff base functionalized Sn complex of the dimethyltin pro-ligand Me ₂ Sn(Quin-py) ₂ (6) was successfully synthesized from 5-[(pyridin-2-ylmethylene)amino]quinolin-8-ol (HQuin-py; 5) in good yield via an alternative strategy exploiting the oxophilic tendencies of tin. All species were fully characterized by NMR (including ¹¹⁹ Sn NMR spectroscopy), HR-ESI MS and single-crystal X-ray diffraction, and preliminary studies of their supramolecular potential are also discussed.

Original language	English
Pages (from-to)	694-699
Number of pages	6
Journal	Zeitschrift fur Anorganische und Allgemeine Chemie
Volume	645
Issue number	9
DOIs	https://doi.org/10.1002/zaac.201900063
Publication status	Published - 15 May 2019

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@article{6acbb16aafb646138dc42190f25e9be8,

title = "The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases",

abstract = " Whilst pursuing the synthetic utility of quinoline-based tin complexes, Me 2 Sn(Quin-NO 2 ) 2 (1) and Ph 2 Sn(Quin-NO 2 ) 2 (2) (Quin-NO 2 = 5-nitroquinolino-8-oate) were synthesized bearing coordinatively inert nitro groups. Conventional reduction methodologies successfully converted 1 to Me 2 Sn(Quin-NH 2 ) 2 (3) and 2 to Ph 2 Sn(Quin-NH 2 ) 2 (4) (Quin-NH 2 = 5-aminoquinolino-8-oate). The synthetically useful amine groups proved difficult to exploit in the presence of the central tin atom, however, a complete Schiff base functionalized Sn complex of the dimethyltin pro-ligand Me 2 Sn(Quin-py) 2 (6) was successfully synthesized from 5-[(pyridin-2-ylmethylene)amino]quinolin-8-ol (HQuin-py; 5) in good yield via an alternative strategy exploiting the oxophilic tendencies of tin. All species were fully characterized by NMR (including 119 Sn NMR spectroscopy), HR-ESI MS and single-crystal X-ray diffraction, and preliminary studies of their supramolecular potential are also discussed.",

keywords = "Coordination chemistry, Main group elements, Quinoline, Schiff bases, Tin",

author = "Butler, {Patrick W.V.} and Ward, {Jas S.}",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = may,

day = "15",

doi = "10.1002/zaac.201900063",

language = "English",

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T1 - The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases

AU - Butler, Patrick W.V.

AU - Ward, Jas S.

PY - 2019/5/15

Y1 - 2019/5/15

N2 - Whilst pursuing the synthetic utility of quinoline-based tin complexes, Me 2 Sn(Quin-NO 2 ) 2 (1) and Ph 2 Sn(Quin-NO 2 ) 2 (2) (Quin-NO 2 = 5-nitroquinolino-8-oate) were synthesized bearing coordinatively inert nitro groups. Conventional reduction methodologies successfully converted 1 to Me 2 Sn(Quin-NH 2 ) 2 (3) and 2 to Ph 2 Sn(Quin-NH 2 ) 2 (4) (Quin-NH 2 = 5-aminoquinolino-8-oate). The synthetically useful amine groups proved difficult to exploit in the presence of the central tin atom, however, a complete Schiff base functionalized Sn complex of the dimethyltin pro-ligand Me 2 Sn(Quin-py) 2 (6) was successfully synthesized from 5-[(pyridin-2-ylmethylene)amino]quinolin-8-ol (HQuin-py; 5) in good yield via an alternative strategy exploiting the oxophilic tendencies of tin. All species were fully characterized by NMR (including 119 Sn NMR spectroscopy), HR-ESI MS and single-crystal X-ray diffraction, and preliminary studies of their supramolecular potential are also discussed.

AB - Whilst pursuing the synthetic utility of quinoline-based tin complexes, Me 2 Sn(Quin-NO 2 ) 2 (1) and Ph 2 Sn(Quin-NO 2 ) 2 (2) (Quin-NO 2 = 5-nitroquinolino-8-oate) were synthesized bearing coordinatively inert nitro groups. Conventional reduction methodologies successfully converted 1 to Me 2 Sn(Quin-NH 2 ) 2 (3) and 2 to Ph 2 Sn(Quin-NH 2 ) 2 (4) (Quin-NH 2 = 5-aminoquinolino-8-oate). The synthetically useful amine groups proved difficult to exploit in the presence of the central tin atom, however, a complete Schiff base functionalized Sn complex of the dimethyltin pro-ligand Me 2 Sn(Quin-py) 2 (6) was successfully synthesized from 5-[(pyridin-2-ylmethylene)amino]quinolin-8-ol (HQuin-py; 5) in good yield via an alternative strategy exploiting the oxophilic tendencies of tin. All species were fully characterized by NMR (including 119 Sn NMR spectroscopy), HR-ESI MS and single-crystal X-ray diffraction, and preliminary studies of their supramolecular potential are also discussed.

KW - Coordination chemistry

KW - Main group elements

KW - Quinoline

KW - Schiff bases

KW - Tin

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DO - 10.1002/zaac.201900063

M3 - Article

SN - 0044-2313

VL - 645

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EP - 699

JO - Zeitschrift fur Anorganische und Allgemeine Chemie

JF - Zeitschrift fur Anorganische und Allgemeine Chemie

IS - 9

ER -

The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases

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