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

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

Istanbul Technical University

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

6 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	4335-4340
Sayfa sayısı	6
Dergi	Tetrahedron
Hacim	73
Basın numarası	30
DOI'lar	https://doi.org/10.1016/j.tet.2017.05.092
Yayın durumu	Yayınlandı - 2017

Bibliyografik not

Publisher Copyright:
© 2017 Elsevier Ltd

Finansman

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

Finansörler
Istanbul Teknik Üniversitesi

Belgeye Erişim

10.1016/j.tet.2017.05.092

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

@article{20f0b001703240ddbd68a3e5960b4a0f,

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",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

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

language = "English",

volume = "73",

pages = "4335--4340",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "30",

}

TY - JOUR

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

UR - https://www.scopus.com/pages/publications/85020201274

U2 - 10.1016/j.tet.2017.05.092

DO - 10.1016/j.tet.2017.05.092

M3 - Article

AN - SCOPUS:85020201274

SN - 0040-4020

VL - 73

SP - 4335

EP - 4340

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

Alıntı Yap