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Traceless solid-phase synthesis of N-substituted 3,5-bis(substituted-idene)piperidin-4-one derivatives

✍ Scribed by Zhang Liu; Jose L. Medina-Franco; Richard A. Houghten; Marc A. Giulianotti

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 166 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.07.072

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✦ Synopsis

A series of N-substituted 3,5-bis(substituted-idene)piperidin-4-ones have been prepared using solidphase organic synthesis. The synthesis starts with a Michael addition with piperidin-4-one serving as the donor and REM resin as the acceptor. Various aldehydes were then utilized through a Knoevenagel condensation to afford the 3,5-bis(substituted-idene)piperidin-4-ones on the solid support. The final products were removed from the support and a second diversity position was introduced through a Hofmann elimination using different alkyl bromides.

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