Abstract
An efficient, simple and one-pot synthesis of pyrimidine derivatives by a three-component reaction of ketones, triethyl orthoformate, and ammonium acetate in the presence of boron sulfuric acid as a reusable and efficient catalyst under solvent-free conditions is reported. The reusability of catalyst, simplicity of the starting materials, short reaction time, one-pot, and good yields of products are the main advantages.
References
1.
Zhu
J.
,
Bienaymé
H.
, Multicomponent reactions. Wiley-VCH , Weinheim, Germanyv , 2005 .
2.
Dömling
A.
, Chem. Rev. , 2006 , 106 , 17 .
3.
Dömling
A.
, and
Ugi
I.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3169 .
4.
Brown
D.J.
,
Evans
R.F.
,
Cowden
W.B.
,
Fenn
M.D.
, Chemistry of heterocyclic compounds: the pyrimidines , Vol. 52 , Wiley-VCH , Weinheim, Germany , 1994 .
5.
Polak
A.
, and
Scholer
H.J.
, Chemotherapy , 1975 , 21 , 113 .
6.
Reddick
J.J.
,
Saha
S.
,
Lee
J.
,
Melnick
J.S.
,
Perkins
J.
, and
Begley
T.P.
, Bioorg. Med. Chem. Lett. , 2001 , 11 , 2245 .
7.
Hertel
L.W.
,
Border
G.B.
,
Kroin
J.S.
,
Rinzel
S.M.
,
Poore
G.A.
,
Todd
G.C.
, and
Grindey
G.B.
, Cancer Res. , 1990 , 50 , 4417
8.
Sherman
W.R.
, and
Taylor
E.C.
, Org. Synth. , 1963 , 4 , 247
9.
Kenner
G.W.
,
Lythgoe
B.
,
Todd
A.R.
, and
Topham
A.
, J. Chem. Soc , 1943 , 388 .
10.
Burgess
D.M.
, J. Org. Chem. , 1956 , 21 , 97
11.
Tyagarajan
S.
, and
Chakravarty
P.K.
, Tetrahedron Lett. , 2005 , 46 , 7889 .
12.
Sasada
T.
,
Kobayashi
F.
,
Sakai
N.
, and
Konakahara
T.
, Org. Lett. , 2009 , 11 , 2161 .
13.
Ghorbani-Vaghei
R.
,
Karimi-Nami
R.
,
Toghraei-Semiromi
Z.
,
Amiri
M.
,
Salimi
Z.
, and
Ghavidel
M.
, C. R. Chim. , 2014 , 17 , 324 .
14.
Salehi
P.
,
Zolfigol
M.A.
,
Shirini
F.
, and
Baghbanzadeh
M.
, Curr. Org. Chem. , 2006 , 10 , 2171 .
15.
Salehi
P.
,
Zolfigol
M.A.
, and
Fard
M.A.
, J. Braz. Chem. Soc , 2004 , 15 , 773 .
16.
Kiasat
A.R.
, and
Fallah-Mehrjardi
M.
, J. Braz. Chem. Soc , 2008 , 19 , 1595 .
17.
Sajjadifar
S.
,
Mirshokraie
S.A.
,
Javaherneshan
N.
,
Louie
O.
, Am. J. Org. Chem. , 2012 , 2 , 1 .
18.
Sajjadifar
S.
,
Khosravani
E.
, and
Shiri
S.
, Int. J. Chem. Tech. Res. , 2013 , 5 , 1969 .
19.
Zolfigol
M.A.
,
Khazaei
A.
,
Vahedi
H.
,
Mokhlesi
M.
,
Sajadifar
S.
, and
Pirveysian
M.
, Phosphorus, Sulfur, Silicon Relat. Elem. , 2012 , 187 , 295 .
20.
Zolfigol
M.A.
,
Vahedi
H.
,
Massoudi
A.H.
,
Sajjadifar
S.
,
Loui
O.
, and
Javaherneshan
N.
, Clin. Biochem. , 2011 , 44 , 219 .