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CCDC-605793 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44(1223)336033; email: deposit@ccdc.cam.ac. uk].
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33748688927
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A base-assisted formal [1,3]-H shift in alkynyl imines 1 into allenyl imines has been proposed as the first step of the cycloisomerization cascade towards pyrroles 2; see ref. 3 for a detailed discussion.
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For the thermal cyclization of alleny 1 thioimine into bicyclic pyrroline derivatives, see: (a) Brandsma, L.; Nedolya, N. A.; Heerma, V.; Van der Kerk, A. S. H. T. M.; Lutz, E. T. H. G.; de Lang, R.-J.; Afonin, A. V.; Trofimov, B. A. Chem. Heterocycl. Compd. (Engl Transl.) 1997, 33, 493.
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3, the solvent was evaporated under reduced pressure, and the residue was purified over a short column of silica gel (hexanes or hexanes-EtOAc) to afford the pure fused pyrroline 4.
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