Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation

Chien Cheng; Yu Chiao Shih; Hui Ting Chen; Tun Cheng Chien

doi:10.1016/j.tet.2012.11.001

Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation

Chien Cheng, Yu Chiao Shih, Hui Ting Chen^*, Tun Cheng Chien

^*Corresponding author for this work

Department of Chemistry

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

19 Citations (Scopus)

Abstract

A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C-H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives.

Original language	English
Pages (from-to)	1387-1396
Number of pages	10
Journal	Tetrahedron
Volume	69
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2012.11.001
Publication status	Published - 2013 Jan 28

Keywords

4-Pyridone
Arylation
C-H activation
Catalysis
Uracil

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.11.001

Cite this

@article{6c8bd627963548c6be6b95cfbdff8e09,

title = "Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation",

abstract = "A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C-H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives.",

keywords = "4-Pyridone, Arylation, C-H activation, Catalysis, Uracil",

author = "Chien Cheng and Shih, {Yu Chiao} and Chen, {Hui Ting} and Chien, {Tun Cheng}",

note = "Funding Information: This work was supported by Research Grants 100-2113-M-003-007-MY2 and 100-2113-M-037-007 - from the National Science Council , Taiwan and NTNU100-D-06 from National Taiwan Normal University . ",

year = "2013",

month = jan,

day = "28",

doi = "10.1016/j.tet.2012.11.001",

language = "English",

volume = "69",

pages = "1387--1396",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation

AU - Cheng, Chien

AU - Shih, Yu Chiao

AU - Chen, Hui Ting

AU - Chien, Tun Cheng

N1 - Funding Information: This work was supported by Research Grants 100-2113-M-003-007-MY2 and 100-2113-M-037-007 - from the National Science Council , Taiwan and NTNU100-D-06 from National Taiwan Normal University .

PY - 2013/1/28

Y1 - 2013/1/28

N2 - A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C-H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives.

AB - A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C-H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives.

KW - 4-Pyridone

KW - Arylation

KW - C-H activation

KW - Catalysis

KW - Uracil

UR - http://www.scopus.com/inward/record.url?scp=84871968634&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84871968634&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.11.001

DO - 10.1016/j.tet.2012.11.001

M3 - Article

AN - SCOPUS:84871968634

SN - 0040-4020

VL - 69

SP - 1387

EP - 1396

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this