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The Synthesis of Quinoline‐based Tin Complexes with Pendant Schiff Bases
Author(s) -
Butler Patrick W. V.,
Ward Jas S.
Publication year - 2019
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201900063
Subject(s) - tin , chemistry , quinoline , schiff base , supramolecular chemistry , ligand (biochemistry) , yield (engineering) , amine gas treating , nitro , synthon , nuclear magnetic resonance spectroscopy , medicinal chemistry , polymer chemistry , combinatorial chemistry , crystal structure , crystallography , stereochemistry , organic chemistry , materials science , alkyl , biochemistry , receptor , metallurgy
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.