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CCDC 689852 (4d), 689853 (4k), 689854 (4c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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CCDC 689852 (4d), 689853 (4k), 689854 (4c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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Preliminary investigations seem to indicate that furoquinolines analogous to 7 are obtained only in those cases where the unsubstituted alkynol, 4-pentyn-1-ol, is used in the presence of aromatic aldehydes, and is independent of the aniline used. Details on this particular reaction will be given separately.
-
Preliminary investigations seem to indicate that furoquinolines analogous to 7 are obtained only in those cases where the unsubstituted alkynol, 4-pentyn-1-ol, is used in the presence of aromatic aldehydes, and is independent of the aniline used. Details on this particular reaction will be given separately.
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The formation of cationic platinum(II) complexes by protonolysis of alkyl or dialkyl platinum complexes has been reported, see: a) T. G. Driver, T. J. Williams, J. A. Labinger, J. E. Bercaw, Organometallics 2007, 26, 294-301;
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2(cod)] under non-protic conditions, we did not observed the formation of the spirofuranquinolines 4 and only starting materials (the alkynol and the imine) were recovered.
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2(cod)] under non-protic conditions, we did not observed the formation of the spirofuranquinolines 4 and only starting materials (the alkynol and the imine) were recovered.
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This reaction could be a catalytic process where the cationic platinum complex acts as a Lewis acid catalyst by activating the imine substrate. For an excellent account on σ- and π-electrophilic Lewis acids, see: Y. Yamamoto, J. Org. Chem. 2007, 72, 7817-7831
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This reaction could be a catalytic process where the cationic platinum complex acts as a Lewis acid catalyst by activating the imine substrate. For an excellent account on σ- and π-electrophilic Lewis acids, see: Y. Yamamoto, J. Org. Chem. 2007, 72, 7817-7831.
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The Brønsted acid catalyzed reaction of enol ethers and aromatic imines to give the corresponding quinoline derivatives is a known process, see: a) D. L. Boger, Comprehensive Organic Synthesis, 5 Eds, B. M. Trost, I. Fleming, Pergamon, Oxford, 1991, pp. 451-512; also see Ref, 5e
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The Brønsted acid catalyzed reaction of enol ethers and aromatic imines to give the corresponding quinoline derivatives is a known process, see: a) D. L. Boger, Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 451-512; also see Ref. [5e].
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