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

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

doi:10.1016/j.tetlet.2010.07.072

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

Zhang Liu
, Jose L. Medina-Franco
, Richard A. Houghten
, Marc A. Giulianotti

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	5003-5004
Number of pages	2
Journal	Tetrahedron Letters
Volume	51
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.072
State	Published - 2010
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by the State of Florida, Executive Office of the Governor’s Office of Tourism, Trade and Economic Development .

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10.1016/j.tetlet.2010.07.072

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

abstract = "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.",

author = "Zhang Liu and Medina-Franco, \{Jose L.\} and Houghten, \{Richard A.\} and Giulianotti, \{Marc A.\}",

note = "Funding Information: This work was supported by the State of Florida, Executive Office of the Governor{\textquoteright}s Office of Tourism, Trade and Economic Development .",

year = "2010",

doi = "10.1016/j.tetlet.2010.07.072",

language = "English (US)",

volume = "51",

pages = "5003--5004",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "38",

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TY - JOUR

T1 - Traceless solid-phase synthesis of N-substituted 3,5-bis(substituted-idene) piperidin-4-one derivatives

AU - Liu, Zhang

AU - Medina-Franco, Jose L.

AU - Houghten, Richard A.

AU - Giulianotti, Marc A.

N1 - Funding Information: This work was supported by the State of Florida, Executive Office of the Governor’s Office of Tourism, Trade and Economic Development .

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/78549287084

UR - https://www.scopus.com/pages/publications/78549287084#tab=citedBy

U2 - 10.1016/j.tetlet.2010.07.072

DO - 10.1016/j.tetlet.2010.07.072

M3 - Article

AN - SCOPUS:78549287084

SN - 0040-4039

VL - 51

SP - 5003

EP - 5004

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

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

Abstract

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