Abstract
A simple, efficient and eco-friendly process for the synthesis in good yield of azoxystrobin from 2-bromophenol has been developed using phenolic hydroxyl protection, Grignard reaction, Suzuki cross-coupling, hydrogenation and a nucleophilic reaction on a 2-chloropyrimidine.
References
1.
Brooke
D.G.
, and
Morris
J. C.
, Tetrahedron Lett. , 2008 , 49 , 2414 .
2.
Howell
C.C.
,
Semple
K. T.
, and
Bending
G. D.
, Chemosphere , 2014 , 95 , 370 .
3.
Yang
F.Q.
,
Zhang
T. Y.
,
Liu
Q. H.
,
Xu
G. Q.
,
Zhang
Y. B.
,
Zhang
S.
, and
Ito
Y.
, J. Chromatogr. A. , 2000 , 883 , 67 .
4.
Zhang
X.
,
Liu
H. J.
,
Gao
Y. X.
,
Wang
H. L.
,
Guo
B. Y.
, and
Li
J. Z.
, Chin. J. Chem. , 2012 , 30 , 1517 .
5.
Javier
P.
,
Josep
M.
,
Consuelo
V.A.
,
Antonio
A. S.
, and
Antonio
A. F.
, Toxicol. Lett. , 2012 , 210 , 240 .
6.
David
A.J.
,
James
P. M.
, and
Mark
R. S.
, Patent, US7084272, 2006 .
7.
Mika
K.
,
Kazuyuki
T.
,
Hiroshi
H.
,
Yukie
Y. M.
,
Mikiko
U.
,
Machiko
S.
,
Eiki
W.
,
Seiji
L.
,
Hiroshi
N.
, and
Shiro
M.
, J. Agr. Food Chem. , 2012 , 60 , 904 .
8.
Zhang
X.
,
Gao
Y. X.
,
Liu
H. J.
,
Guo
B. Y.
, and
Wang
H. L.
, Bull. Korean Chem. Soc. , 2012 , 33 , 2627 .
9.
Dilip K
P.
,
Sandip
D.
,
Kamal R
C.
,
Mayur V
K.
,
Bhalachandra M
B.
, and
Vimal K
J.
, Tetrahedron Lett. , 2014 , 55 , 2953 .
10.
Mansoor
I.H.
,
Nasir
R.
,
Gulraiz
A.
,
Abbas
C. G.
,
Ghulam
M. S.
,
Muhammad
Z.
,
Ali
R. U.
,
Muhammad
Z. U. H.
, and
Ze
J. H.
, Molecules , 2015 , 20 , 5202 .
11.
Johnson
C.R.
,
Adams
J. P.
,
Braun
M. P.
,
Senanayake
C. B. W.
,
Wovkulich
P. M.
, and
Uskokovlc
M. R.
, Tetrahedron Lett. , 1992 , 33 , 917 .
12.
Miyaura
N.
, and
Suzuki
A.
, Chem. Rev. , 1995 , 95 , 2457 .
13.
Peshkov
A.A.
,
Peshkov
V. A.
, and
Pereshivko
O. P.
, J. Org. Chem. , 2015 , 80 , 6598 .
14.
Coleman
R.S.
, and
Lu
X. L.
, Chem. Commun. , 2006 , 4 , 423 .
15.
Clough
J.M.
, and
Godfrey
C. R. A.
, Patent, EP260794, 1988 .
16.
Yang
P.
,
Liu
Y. K.
, and
Xu
Z. Y.
, World Pesticides , 2013 , 35 , 26 .
17.
Christensen
H.B.
, and
Granby
K.
, Food Addit. Contam. A. , 2011 , 18 , 866 .