Journal
TETRAHEDRON
Volume 68, Issue 9, Pages 2146-2154Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.01.016
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Funding
- Council for Scientific and Industrial Research, New Delhi
- Department of Science and Technology, New Delhi
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Syntheses of a variety of aza-polycycles employing 2-(N-allylaminomethyl)cinnamaldehydes derived from Morita-Baylis-Hillman adducts of acrylates via intramolecular 1,3-dipolar cycloaddition, or Aza-Diels Alder or domino Knoevenagel/hetero Diels Alder cycloaddition reactions are described. Whereas the Aza-Diels Alder afforded a mixture of cis- and trans-isomers of substituted 1,2,3,4,4a,5,10,10a-octahydrobenzo[b][1,6]naphthyridines, the 1,3-dipolar cycloaddition and domino Knoevenagel/hetero Diels Alder were diastereoselective to produce exclusively cis-derivatives of 1,2,3,4,4a,6,7,8,9,9a-decahydro-1H-pyrido[3,4-b]pyrrolizine-8a-carboxylates and 3,4,4a,5,7,8,9,10b-octahydro-1H-chromeno[3,4-c]pyridin-10(2H)-ones, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
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