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Synlett 2003(15): 2301-2304  
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

Céline Simona, Frédéric Lieby-Mullera, Jean-François Peyronelb, Thierry Constantieux*a, Jean Rodriguez*a
a Laboratoire RéSo, Réactivité en Synthèse organique, UMR au CNRS 6516, Centre de St Jérôme, boîte D12, 13397 Marseille cedex 20, France
Fax: +33(491)288841; e-Mail: Jean.Rodriguez@univ.u-3mrs.fr;
b Aventis Pharma, Département de Chimie Médicinale, Centre de Recherches de Paris, 13 Quai Jules Guesde- BP-14, 94403 Vitry-sur-Seine, France
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Publication History

Received 2 September 2003
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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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.