M. L. Deb, P. J. Bhuyan / Tetrahedron Letters 46 (2005) 6453–6456
6455
Table 3 (continued)
Produts
6/7/8/9
RCHO
Time (min)
15
Yield (%)
87
Mp (°C)
O
CHO
HN
17
268 (dec)
10f
O
N
H
O
O
O
HN
17
10g
10h
10i
11
30
60
30
2
80
60
60
94
264
CHO
O
O
N
H
CHO
O
O
149–152
127–129
139–141
O
O
O
CH3
H CO
CHO
3
O
Me
CHO
OH
N
O
N
OMe
Ph
excellent results in all cases and our observations are
recorded in Table 3.
6. Prajapati, D.; Lekhok, K. C.; Sandhu, J. S.; Ghosh, A. C.
J. Chem. Soc., Perkin Trans. 1 1996, 959–960.
7
8
9
. Bose, D. S.; Narsaiah, A. V. J. Chem. Res. (S) 2001, 36–
8.
. Reddy, T. I.; Verma, R. S. Tetrahedron Lett. 1997, 38,
721–1724.
. (a) Kubota, Y.; Nishizaki, Y.; Ikeya, H.; Saeki, M.; Hida,
T.; Kawazu, S.; Yoshida, M.; Fujii, H.; Sugi, Y. Micro-
porous Mesoporous Mater. 2004, 70, 135–149; (b) Ben-
nazha, J.; Zahouilly, M.; Boukhari, A.; Hol, E. A. J. Mol.
Catal. A: Chem. 2003, 202, 247–252.
3
In conclusion, we have demonstrated a very simple and
highly efficient method for the condensation of aromatic
and heteroaromatic aldehydes with various active meth-
ylene compounds to give Knoevenagel products in excel-
lent yields. We suggest that the present method may
displace all other methods that use various organic sol-
vents, catalysts and that are performed at high
temperature.
1
10. (a) Harjani, J. R.; Nara, S. J.; Salunkhe, M. M. Tetra-
hedron Lett. 2002, 43, 1127–1130; (b) Khan, F. A.; Dash,
J.; Satapathy, R.; Upadhyaya, S. K. Tetrahedron Lett.
2
004, 45, 3055–3058.
Acknowledgement
1
1. (a) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous
Media; John Wiley and Sons: New York, 1997, 1–189; (b)
Lindstrom, U. M. Chem. Rev. 2002, 102, 2751–2772.
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L.; Maggi, R.; Piccinno, A.; Sartori, G. Green Chem. 2001,
3, 101–104; (c) Hangarge, R. V.; Sonwane, S. A.; Jarikotc,
D. V.; Shingarce, M. S. Green Chem. 2001, 3, 310–312; (d)
Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Tetra-
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Mohit L. Deb thanks CSIR, New Delhi, for the award
of a Junior Research Fellowship.
1
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