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0347182020
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note
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This 2D NMR study is part of: C. Simon; PhD Thesis; University Aix-Marseille III: France, 2001; and details will be published soon in a full paper.
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31
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0036795290
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The Michael adduct can be obtained by reaction of 1 with acroleine in the presence of Dowex resins. When this 1,5-dicarbonyl intermediate reacts with primary amines, related naphthyridine derivatives 4 and azabicyclo[3.3.1] nonanones 5 are formed. For more experimental details, see: Simon, C.; Peyronel, J.-F.; Clerc, F.; Rodriguez, J. Eur. J. Org. Chem. 2002, 3359.
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Rodriguez, J.4
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32
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0029856245
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Under these reaction conditions, another mechanistic pathway involving an imine resulting from acrolein and primary amine may be postulated. Nevertheless, although it is known that acyclic 1,3-dicarbonyls react with 3-substituted 1-aza-1,3-butadienes under acidic conditions, it has also been reported that simple enimines derived from acrolein or α,β- unsaturated ketones were not isolable. Therefore, these imines are likely not to be reactive intermediates in our MCR. For more details on such reported results, see: Geirsson, J. K. F.; Johannesdottir, J. F. J. Org. Chem. 1996, 61, 7320.
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