Abstract
A series of methyl ethyl 2,6-dimethyl-4-substituted-1,4-dihydropyridine-3,5-dicarboxylates were synthesised by the three-component reaction of aldehydes, ethyl acetoacetate and methyl β-aminocrotonate in the presence of triethylbenzylammonium chloride (TEBAC) in aqueous medium. This method has the advantage of good yields.
References
1.
Amato
J.
, Science , 1993 , 259 , 1538 .
2.
Illman
D.L.
, Chem. Eng. News , 1993 , 71 , 5 .
3.
Illman
D.L.
, Chem. Eng. News , 1994 , 72 , 22 .
4.
Li
C.J.
, and
Chang
T.H.
, Organic reactions in aqueous media , Wiley , New York , 1997 .
5.
Fringuelli
F.
,
Piematti
O.
,
Pizzo
F.
, and
Vaccaro
L.
, Eur. J. Org. Chem. , 2001 , 439 .
6.
Stinson
S.C.
, Chem. Eng. News , 1996 , 74 , 39 .
7.
Breslow
R.
, and
Rideout
D.C.
, J. Am. Chem. Soc. , 1980 , 102 , 1816 .
8.
Breslow
R.
, Acc. Chem. Res. , 1991 , 24 , 59 .
9.
Li
C.J.
, Chem. Rev. , 1993 , 93 , 2023 .
10.
Ballini
R.
, and
Bosica
G.
, Tetrahedron Lett. , 1996 , 37 , 8027 .
11.
Ballini
R.
,
Bosica
G.
, and
Mecozzi
T.
, Tetrahedron , 1997 , 53 , 1341 .
12.
Meijer
A.
,
Otto
S.
, and
Engberts
J.B.F.N.
, J. Org. Chem. , 1998 , 63 , 8989 .
13.
Bigi
F.
,
Chesini
L.
,
Maggi
R.
, and
Sartori
G.
, J. Org. Chem. , 1999 , 64 , 1033 .
14.
Bigi
F.
,
Carloni
S.
,
Ferrari
L.
,
Maggi
R.
,
Mazzacani
A.
, and
Sartori
G.
, Tetrahedron Lett. , 2001 , 42 , 5203 .
15.
Fringuelli
F.
,
Pani
G.
,
Piermatti
O.
, and
Pizzo
F.
, Tetrahedron , 1994 , 50 , 1499 .
16.
Janis
R.A.
,
Silver
P.J.
, and
Triggle
D.J.
, Adv. Drug. Res. , 1987 , 16 , 30 .
17.
Christiaans
J.A.M.
,
Windhorst
A.D.
,
Gronenberg
P.M.
,
van der Goot
H.
, and
Timmerman
H.
, Eur. J. Med. Chem. , 1993 , 28 , 859 .
18.
Christiaans
J.A.M.
, and
Timmerman
H.
, Eur. J. Pharm. Sci. , 1996 , 4 , 1 .
19.
Janis
R.A.
, and
Triggle
D.J.
, J. Med. Chem. , 1983 , 26 , 773 .
20.
Lawson
J.E.
, Bioorg. Med. Chem. Lett. , 1993 , 3 , 561 .
21.
Mahendra
M.
,
Doreswamy
B.H.
,
Manvar
D.
,
Patel
G.
,
Naliapara
Y.
,
Shah
A.
,
Anandalwar
S.M.
, and
Prasad
J.S.
, J. Chem. Res. (S ), 2004 , 843 .
22.
Shah
A.C.
,
Arya
V.P.
, and
Sainani
J.B.
, Ind. J. Chem. , 1995 , 34B , 17 .
23.
van Rhee
A.M.
,
Jiang
J.
,
Melman
N.
,
Olah
M.E.
,
Stiles
G.L.
, and
Jacobson
K.A.
, J. Med. Chem. , 1996 , 39 , 2980 .
24.
Hantzsch
A.
, Justus Liebigs Ann. Chem. , 1882 , 215 , 1
25.
Gordeev
M.F.
,
Patel
D.V.
, and
Gordon
E.M.
, J. Org. Chem. , 1996 , 61 , 924 .
26.
Breitenbucher
J.G.
, and
Figliozzi
G.
, Tetrahedron Lett. , 2000 , 41 , 4311 .
27.
Ohberg
L.
, and
Westman
J.
, Synlett , 2001 , 1296 .
28.
Anderson
A.G.J.
, and
Berkelhammer
G.
, J. Am. Chem. Soc. , 1958 , 80 , 992 .
29.
Phillips
A.P.
, J. Am. Chem. Soc. , 1949 , 71 , 4003 .
30.
Maquestiau
A.
,
Maeyence
A.
, and
Vanden Eynde
J.J.
, Tetrahedron Lett. , 1991 , 32 , 3839 .
31.
Sabitha
G.
,
Kiran Kumar Reddy
G.S.
,
Srinivas
C.
, and
Yadav
J.S.
, Tetrahedron Lett. , 2003 , 44 , 4129 .
32.
Salehi
H.
, and
Guo
Q.X.
, Synth. Commun. , 2004 , 34 , 4349 .
33.
Xia
J.J.
, and
Wang
G.W.
, Synthesis , 2005 , 2379 .
34.
Wang
G.W.
,
Xia
J.J.
,
Miao
C.B.
, and
Wu
X.L.
, Bull. Chem. Soc. Jpn. , 2006 , 79 , 454 .
35.
Memarian
H.R.
,
Abdoli-Senejani
M.
, and
Döpp
D.
, Z. Naturforsch. , 2006 , 61b , 50 .
36.
Khadilkar
B.M.
,
Gaikar
V.G.
, and
Chitnavis
A.A.
, Tetrahedron Lett. , 1995 , 36 , 8083 .
37.
Shi
D.Q.
,
Mou
J.
,
Zhuang
Q.Y.
,
Wang
X.S.
, and
Tu
S.J.
, Chin. J. Org. Chem. , 2004 , 24 , 1042 .
