DABCO catalyzed a convenient synthesis of 1-[5-(8hydroxyquinolin-5-yl)-1-alkyl (aryl)-2-methyl-1Hpyrrol-3-yl]ethanone in aqueous medium.
Shawkat A. abdel-Mohsen
Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt.
E-mail: Shawk662001@yahoo.com.
A green and simple method to synthesis of 1-[5-(8-hydroxyquinolin-5-yl)-1-alkyl (aryl)-2methyl-1H-pyrrol-3-yl]ethanone (4) via the reaction of 5-chloroacetyl-8-hydroxyquinoline
(1) pentane-2,4-dione (2) and amines (3) in the presence of a catalytic amount of
DABCO
1-4
at 70 oC. The procedure is amenable for the synthesis of new substituted
pyrroles. Moreover, short reaction time environmentally friendly procedure and excellent
yields are the main advantages of this procedure which makes it more economic than
other environmental methods.
N
N
HO
O
Cl
O
1
+
O
H3C
HO
CH3
2
+
R
NH2
3
DABCO
0
H2O/ 70 C
COCH3
4
R = alkyl / aryl
N
R
Referrences:
1.
R. A. Jones and G. P. Bean, “The Chemistry of Pyrroles,” Academic Press, London, 1977.
2.
X. Bu, H. Jing, L. Wang, T. Chang, L. Jin and Y. Liang, Journal of Molecular Catalysis A: Chemical,
Vol. 259, No. 1-2, 2006, pp. 121-124.
3.
T. Sharafi and M. M. Heravi, Phosphorus, Sulfur Silicon, Vol. 179, No. 12, 2004, pp. 2437-2440
4.
H. Mitaram Meshram*, V. Madhukar Bangade, B.Chennakesava Reddy, G. Santosh Kumar,
P.Bhagwan Thakur, International Journal of Organic Chemistry, 2012, 2, 159-165
CH3