Amberlyst-15 catalyzed Michael addition of β-dicarbonyl compounds to the enones and unexpected ring closure products

Hande Gunduz; Hamdiye Ece; Armagan Atsay; Volkan Kumbaraci; Naciye Talinli

doi:10.1016/j.tet.2017.05.092

Amberlyst-15 catalyzed Michael addition of β-dicarbonyl compounds to the enones and unexpected ring closure products

Hande Gunduz, Hamdiye Ece, Armagan Atsay, Volkan Kumbaraci^*, Naciye Talinli

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

5 Citations (Scopus)

Abstract

Conjugate addition reactions of 2,4-pentandione, dibenzoylmethane and ethylacetoacetate to enones have been investigated using Amberlyst-15 or Amberlyst-15-DMAP acetate system as catalysts. When 2,4-pentandione reactions were carried out in the presence of Amberlyst-15, conjugate addition and/or conjugate-addition initiated ring closure products were obtained depending on the reaction conditions. However, unlike 2,4-pentandione, dibenzoylmethane gave only conjugate addition products with Amberlyst-15. When Amberlyst-15-DMAP acetate system was used, always only conjugate addition products were obtained with β-dicarbonyl compounds independent of the reaction conditions.

Original language	English
Pages (from-to)	4335-4340
Number of pages	6
Journal	Tetrahedron
Volume	73
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2017.05.092
Publication status	Published - 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

Funding

We are grateful to Istanbul Technical University research fund for financial support.

Funders	Funder number
Istanbul Teknik Üniversitesi

Keywords

Amberlyst-15
DMAP acetate
Michael addition
Ring closure
β-Dicarbonyl compounds

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10.1016/j.tet.2017.05.092

Cite this

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title = "Amberlyst-15 catalyzed Michael addition of β-dicarbonyl compounds to the enones and unexpected ring closure products",

abstract = "Conjugate addition reactions of 2,4-pentandione, dibenzoylmethane and ethylacetoacetate to enones have been investigated using Amberlyst-15 or Amberlyst-15-DMAP acetate system as catalysts. When 2,4-pentandione reactions were carried out in the presence of Amberlyst-15, conjugate addition and/or conjugate-addition initiated ring closure products were obtained depending on the reaction conditions. However, unlike 2,4-pentandione, dibenzoylmethane gave only conjugate addition products with Amberlyst-15. When Amberlyst-15-DMAP acetate system was used, always only conjugate addition products were obtained with β-dicarbonyl compounds independent of the reaction conditions.",

keywords = "Amberlyst-15, DMAP acetate, Michael addition, Ring closure, β-Dicarbonyl compounds",

author = "Hande Gunduz and Hamdiye Ece and Armagan Atsay and Volkan Kumbaraci and Naciye Talinli",

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year = "2017",

doi = "10.1016/j.tet.2017.05.092",

language = "English",

volume = "73",

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T1 - Amberlyst-15 catalyzed Michael addition of β-dicarbonyl compounds to the enones and unexpected ring closure products

AU - Gunduz, Hande

AU - Ece, Hamdiye

AU - Atsay, Armagan

AU - Kumbaraci, Volkan

AU - Talinli, Naciye

PY - 2017

Y1 - 2017

N2 - Conjugate addition reactions of 2,4-pentandione, dibenzoylmethane and ethylacetoacetate to enones have been investigated using Amberlyst-15 or Amberlyst-15-DMAP acetate system as catalysts. When 2,4-pentandione reactions were carried out in the presence of Amberlyst-15, conjugate addition and/or conjugate-addition initiated ring closure products were obtained depending on the reaction conditions. However, unlike 2,4-pentandione, dibenzoylmethane gave only conjugate addition products with Amberlyst-15. When Amberlyst-15-DMAP acetate system was used, always only conjugate addition products were obtained with β-dicarbonyl compounds independent of the reaction conditions.

AB - Conjugate addition reactions of 2,4-pentandione, dibenzoylmethane and ethylacetoacetate to enones have been investigated using Amberlyst-15 or Amberlyst-15-DMAP acetate system as catalysts. When 2,4-pentandione reactions were carried out in the presence of Amberlyst-15, conjugate addition and/or conjugate-addition initiated ring closure products were obtained depending on the reaction conditions. However, unlike 2,4-pentandione, dibenzoylmethane gave only conjugate addition products with Amberlyst-15. When Amberlyst-15-DMAP acetate system was used, always only conjugate addition products were obtained with β-dicarbonyl compounds independent of the reaction conditions.

KW - Amberlyst-15

KW - DMAP acetate

KW - Michael addition

KW - Ring closure

KW - β-Dicarbonyl compounds

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U2 - 10.1016/j.tet.2017.05.092

DO - 10.1016/j.tet.2017.05.092

M3 - Article

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SN - 0040-4020

VL - 73

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JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Amberlyst-15 catalyzed Michael addition of β-dicarbonyl compounds to the enones and unexpected ring closure products

Abstract

Bibliographical note

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Keywords

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