A New Multicomponent Domino Reaction of 1,3-Dicarbonyl Compounds: One-Pot Access to Amino Azabicyclo[3.3.1]nonanones and 1,6-Hydro­naphthyridines

Abstract

Depending on the structure of amine, the multicomponent Domino reaction of β-ketoester 1 with acrolein 2 and various primary amines 3, in the presence of 4Å MS, leads either to 1,6-hydronaphthyridines 4 or amino azabicyclo[3.3.1]nonanones 5 in a one-pot sequence. The stereoselective reduction of compounds 4 to provide new functionalized 1,6-trans-diazadecalins 6 is also reported.

Key words

1,3-dicarbonyls - multicomponent domino reaction - Michael addition - azabicyclo[3.3.1]nonanes - 1,6-hydronaphthyridines - 1,6-trans-diazadecalins

References

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• 30 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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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.