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Synthesis 2002(1): 0116-0120
DOI: 10.1055/s-2002-19304
DOI: 10.1055/s-2002-19304
PAPER
© Georg Thieme Verlag Stuttgart · New York
MIRC Reactions of (E)-Chalcones with Azol-5-ones - A Diastereoselective Entry to Novel Spiro Tetrahydropyridine Derivatives
Further Information
Received
16 August 2001
Publication Date:
04 August 2004 (online)
Publication History
Publication Date:
04 August 2004 (online)
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Abstract
Spiro tetrahydropyridine derivatives 4 and 5 were diastereoselectively prepared in good yield by reacting chalcones 3 with azolin-5-ones 1 and 2. From benzalacetones 10, the reaction occurred only with isoxazolin-5-ones 1 leading to spirans 11.
Key words
chalcones - spiro compounds - diastereoselectivity - Michael additions
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References
The use of substituted benzaldehydes in both these procedures was unsuccessful, indicating that steric or electronic factors can play a negative role in the transformations of 1 or 2 to 4 or 5 respectively, which is not the case with isoxazolin-5-one 1.