Transformation of a hydroxyl into an acyl group on α-pyrone ring: A novel route to 3,4-diacylcoumarins

Antigoni Kotali; Despina A. Nasiopoulou; Philip A. Harris; Madeleine Helliwell; John A. Joule

doi:10.1016/j.tet.2011.10.086

Transformation of a hydroxyl into an acyl group on α-pyrone ring: A novel route to 3,4-diacylcoumarins

Antigoni Kotali^*, Despina A. Nasiopoulou, Philip A. Harris, Madeleine Helliwell, John A. Joule

^*Corresponding author for this work

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

Abstract

The transformation of a hydroxyl into an acyl group, a transformation which has been extensively investigated on the benzene nucleus of several substrates, is now applied successfully for the first time to a heterocyclic ring and specifically to the pyrone ring of coumarin to yield novel 3,4-diacylcoumarins in good yields. The reaction involves formation of a new C-C bond.

Original language	English
Pages (from-to)	761-766
Number of pages	6
Journal	Tetrahedron
Volume	68
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2011.10.086
Publication status	Published - 14 Jan 2012

Keywords

3,4-Diacylcoumarins
4-Hydroxycoumarin
Acylhydrazones
C-C bond formation
Diacetoxyiodoso benzene
Lead tetraacetate

Access to Document

10.1016/j.tet.2011.10.086

Cite this

@article{5f31499ab14b4efebfd4321d179827d2,

title = "Transformation of a hydroxyl into an acyl group on α-pyrone ring: A novel route to 3,4-diacylcoumarins",

abstract = "The transformation of a hydroxyl into an acyl group, a transformation which has been extensively investigated on the benzene nucleus of several substrates, is now applied successfully for the first time to a heterocyclic ring and specifically to the pyrone ring of coumarin to yield novel 3,4-diacylcoumarins in good yields. The reaction involves formation of a new C-C bond.",

keywords = "3,4-Diacylcoumarins, 4-Hydroxycoumarin, Acylhydrazones, C-C bond formation, Diacetoxyiodoso benzene, Lead tetraacetate",

author = "Antigoni Kotali and Nasiopoulou, {Despina A.} and Harris, {Philip A.} and Madeleine Helliwell and Joule, {John A.}",

year = "2012",

month = jan,

day = "14",

doi = "10.1016/j.tet.2011.10.086",

language = "English",

volume = "68",

pages = "761--766",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier BV",

number = "2",

}

TY - JOUR

T1 - Transformation of a hydroxyl into an acyl group on α-pyrone ring

T2 - A novel route to 3,4-diacylcoumarins

AU - Kotali, Antigoni

AU - Nasiopoulou, Despina A.

AU - Harris, Philip A.

AU - Helliwell, Madeleine

AU - Joule, John A.

PY - 2012/1/14

Y1 - 2012/1/14

N2 - The transformation of a hydroxyl into an acyl group, a transformation which has been extensively investigated on the benzene nucleus of several substrates, is now applied successfully for the first time to a heterocyclic ring and specifically to the pyrone ring of coumarin to yield novel 3,4-diacylcoumarins in good yields. The reaction involves formation of a new C-C bond.

AB - The transformation of a hydroxyl into an acyl group, a transformation which has been extensively investigated on the benzene nucleus of several substrates, is now applied successfully for the first time to a heterocyclic ring and specifically to the pyrone ring of coumarin to yield novel 3,4-diacylcoumarins in good yields. The reaction involves formation of a new C-C bond.

KW - 3,4-Diacylcoumarins

KW - 4-Hydroxycoumarin

KW - Acylhydrazones

KW - C-C bond formation

KW - Diacetoxyiodoso benzene

KW - Lead tetraacetate

UR - http://www.scopus.com/inward/record.url?scp=82955237589&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2011.10.086

DO - 10.1016/j.tet.2011.10.086

M3 - Article

AN - SCOPUS:82955237589

SN - 0040-4020

VL - 68

SP - 761

EP - 766

JO - Tetrahedron

JF - Tetrahedron

IS - 2

ER -

Transformation of a hydroxyl into an acyl group on α-pyrone ring: A novel route to 3,4-diacylcoumarins

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

CCDC 847443: Experimental Crystal Structure Determination

Cite this

Transformation of a hydroxyl into an acyl group on α-pyrone ring: A novel route to 3,4-diacylcoumarins

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 847443: Experimental Crystal Structure Determination

Cite this