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Synlett 2003(15): 2301-2304
DOI: 10.1055/s-2003-42121
DOI: 10.1055/s-2003-42121
LETTER
© Georg Thieme Verlag Stuttgart · New York
A New Multicomponent Domino Reaction of 1,3-Dicarbonyl Compounds: One-Pot Access to Amino Azabicyclo[3.3.1]nonanones and 1,6-Hydronaphthyridines
Further Information
Received
2 September 2003
Publication Date:
07 November 2003 (online)
Publication History
Publication Date:
07 November 2003 (online)
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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
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References
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.