Jul-Aug 2007
Microwave Assisted Synthesis of Coumarins Via Potassium Carbonate
869
Catalyzed Knoevenagel Condensation
8
.95(s,1H,olefinic CH), 11.15(1H, s, OH), IR, ꢀ (KBr disc): 3300-
REFERENCES:
-1
+
3100, 1725,1685 cm , EIMS (70ev) m/z: (M 234), Anal. Calcd.
for C H O : C, 61.53%; H, 4.27%; found C, 60.98%; H, 4.20%.
12
10
5
*
Corresponding author. Fax: +98-412-4524991. e-mail:
1
1
e: HNMR ꢁ (DMSO d ): 4.15(s, 3H, OMe), 6.71(d, 1H,
6
ArH), 6.72(dd, 1H, ArH), 7.17(dd, 1H, ArH), 8.68(s,1H,olefinic
[1] O'Kennedy R.; Thornes R. D. Coumarins: Biology,
Applications and Mode of Action, John Wiley & Sons, Chichester, 1997.
CH), 11.25(1H, s, OH), IR, ꢀ (KBr disc): 3305-3150, 1725,1685
-
1
+
[
2] Zahradnik M. The Production and Application of Fluorescent
cm , EIMS (70ev) m/z: (M 220), Anal. Calcd. for C H O : C,
1
1
8
5
Brightening Agents, John Wiley & Sons, 1992.
6
0.00%; H, 3.63%; found C, 59.40%; H, 3.50%.
1
[3a] Irena Kostova, Current Medicinal Chemistry - Anti-Cancer
Agents, 2005, 5, 29. [b] Lakin K. M.; Smirnova T. V.; Vishnyakova G.
M.; Lobanova E. G. ; Novikova N. V.; Sklyarenko V. I. Pharmaceutical
Chemistry Journal, 1989, 23, 824.
[4] Murray R. D. H.; Mendez J.; Brown S. A. The Natural
Coumarins: Occurance, Chemistry and Biochemistry, John Wiley &
Sons, New York, 1982.
1
f: HNMR ꢁ (DMSO d ): 6.69(d, 1H, ArH), 6.70(dd, 1H,
6
ArH), 7.15(dd, 1H, ArH), 8.35(s,1H, olefinic CH), 11.05(1H, s,
-1
OH), IR, ꢀ (KBr disc): 3300-3140, 2220, 1675 cm , EIMS
+
(
70ev) m/z: (M 187), Anal. Calcd. for C H NO : C, 67.11%; H,
10 5 3
2
.67%; N, 7.48%; found C, 66.60%; H, 2.61%; N, 7.41%.
1
1
g: HNMR ꢁ (CDCl ): 1.13(t, 6H, N(CH Me) ), 1.41(t, 3H,
3 2 2
[
5a] Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; [b] Jie
OCH Me), 3.39(q, 4H, N(CH Me) ), 4.45(q, 2H, OCH2), 6.55(d,
2
2
2
Wu, Chemistry Letters, 2006, 35(1), 118; [c] Heravi M.; Hekmatshoar
R.; Emamgholizadeh M. Phosphorus, Sulfur, and Silicon and the
Related Elements, 2004, 179(9), 1893.
1
H, ArH), 6.57(dd, 1H, ArH), 7.15(d, 1H, ArH), 8.95(s, 1H,
-1
olefinic CH), ); IR, ꢀ (KBr disc): 1735, 1687 cm , EIMS (70ev)
m/z: (M 289), Anal. Calcd. for C H NO : C, 66.43%; H,
+
1
6
19
4
[
6a] Loupy, A.; Top. Curr. Chem. 2000, 206, 153; [b] W. Bao; Z.
6
.57%; N, 4.84%; found C, 65.92%; H, 6.30%; N, 4.72%.
Wang; Li Y. Journal of Chemical Research, 2003, 5, 294.
[7] Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media,
John Wiley & Sons: New York, 1997.
1
1
h: HNMR ꢁ (CDCl ): 1.23(t, 6H, N(CH Me) ), 3.33(q, 4H,
3 2 2
N(CH Me) ), 2.76(s, 3H, Me), 6.56(d, 1H, ArH), 6.57(dd, 1H,
2
2
ArH), 7.17(d, 1H, ArH), 8.73(s, 1H, olefinic CH), ); IR, ꢀ (KBr
disc): 1732, 1672 cm , EIMS (70ev) m/z: (M 259), Anal.
[8] Grieco, P. A. Ed. Organic Synthesis in Water; Blackie
Academic and Professional, London, 1998.
-1
+
[
9] Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1.
10] Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and
Practice, Oxford University Press, Oxford, 1998.
11] Rao, P. S.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32,
821.
12] de la Cruz P.; Díez-Barra, E.; Loupy, A.Langa, F.
Calcd. for C H NO : C, 69.49%; H, 6.56%; N, 5.40%; found
15
17
3
[
C, 68.25%; H, 6.26%; N, 5.28%.
1
1
i: HNMR ꢁ (CDCl ): 1.47(t, 3H, Me), 4.38(q, 2H, OCH2),
3
[
3
7
1
.68(3H, s, OMe), 6.82(dd, 1H, ArH), 7.10(dd, 1H, ArH),
5
.18(dd, 1H, ArH), 8.74(s,1H,olefinic CH), IR, ꢀ (KBr disc):
[
-
1
+
718,1690 cm , EIMS (70ev) m/z: (M 248), Anal. Calcd. for
Tetrahedron Lett. 1996, 37, 111.
C H O : C, 62.90%; H, 4.83%; found C, 62.06%; H, 4.70%.
[13] Balalaie, S.; Nemati, N. Synth. Commun. 2000, 30, 869.
[14] Jones G. Organic Reactions, 1967, 15, 204.
15a] Villemin D.; Martin B. Synthetic. Commun.,1998, 28, 3201;
13
12
1
5
1
j: HNMR ꢁ (CDCl ): 2.75(s, 3H, Me), 3.65(3H, s, OMe),
3
[
6
8
.83(dd, 1H, ArH), 7.11(dd, 1H, ArH), 7.17(dd, 1H, ArH),
-1
[b] Bogdal D. J. Chem. Research (S), 1998, 468.
.72(s,1H,olefinic CH), IR, ꢀ (KBr disc): 1715,1677 cm , EIMS
+
[16a] Ayoubi S. A.; Texier-Boullet F.; Hamelin D. Synthesis, 1994,
58; [b] Kim S. Y.; Kwon P. S.; Kwon T. W. Synth. Commun., 1997,
7, 533; [c] Kim J. K.; Kwon P. S.; Kwon T. W. Synth. Commun., 1996,
(70ev) m/z: (M 218), Anal. Calcd. for C H O : C, 66.05%; H,
12 10 4
2
2
4
.58%; found C, 65.55%; H, 4.41%.
1
2
a: HNMR ꢁ (CDCl ): 1.37(t, 3H, Me), 4.35(q, 2H, OCH2),
3
26, 535.
6
1
.98(d, 1H, ArH), 7.29(m, 1H, ArH), 7.38(m, 1H, ArH), 7.58(d,
H, ArH), 7.61(dd, 1H, ArH), 7.72(dd, 1H, ArH), 9.32(s, 1H,
[
17] Bose A. K.; Manhas M. S.; Ghosh M.; Raju V. S.; Tabei K.;
Urbanczyk-Lipkowska Z. Heterocylces, 1990, 30, 741.
[18a] Boon J. A.; Levisky J. A.; Pflug J. L. and Wilkes J.S. J. Org.
Chem. 1986, 51, 480; [b] Earle M. J.; Adams C. H.; Roberts G. and
Seddon K. R. J. Chem. Soc. Chem. Commun. 1998, 19, 2097; [c] Song
C. E.; Shim W. H.; Roh E. J. and Chol J. H. J. Chem. Soc. Chem.
Commun. 2000, 17, 1695.
19a] Schofer S. H.; Kaftzik N.; Wasserscheid P. and Kragl U. J.
Chem. Soc. Chem. Commun. 2001, 5, 425.
20a] Saurez P. A.; Dullius J. E.; Einloft S.; De Souza R. F. and
-1
olefinic CH), ); IR, ꢀ (KBr disc): 1745, 1680 cm , EIMS (70ev)
m/z: (M 268), Anal. Calcd. for C H O : C, 71.64%; H, 4.47%;
found C, 71.15%; H, 4.39%.
+
16
12
4
1
2
b: HNMR ꢁ (CDCl ): 2.75(s, 3H, Me), 7.01(d, 1H, ArH),
3
7.32(m, 1H, ArH), 7.41(m, 1H, ArH), 7.62(d, 1H, ArH), 7.66(dd, 1H,
[
ArH), 7.76(dd, 1H, ArH), 9.21(s, 1H, olefinic CH), ); IR, ꢀ (KBr
disc): 1705, 1679 cm , EIMS (70ev) m/z: (M 267), Anal. Calcd. for
-1
+
[
C H O : C, 75.63%; H, 4.20%; found C, 75.05%; H, 4.15%.
Dupont J. Polyhedron 1996, 15, 1217; [b] Dyson P. J.; Ellis D. J.; Parker
D. G.; Welton T. J. Chem. Soc. Chem. Commun. 1999, 1, 25.
15
10
3
1
2
c: HNMR ꢁ (CDCl ): 7.12(d, 1H, ArH), 7.35(m, 1H, ArH),
3
7
7
2
.42(m, 1H, ArH), 7.61(d, 1H, ArH), 7.67(dd, 1H, ArH),
[21] Khadilkar B. M.; Rebeiro G. L. Synth. Commun. 2000, 30,
1
605.
[22] Hisahiro H.; Yumiko S.; Takashi H.; Toshio S.; Masayoshi
A.; Keisuke O. and Chiaki Y. Tetrahedron Lett. 2001, 42, 4349.
23] Khadilkar B. M. and Rebeiro G. L. Synthesis 2001, 3, 370.
24a] Valizadeh H.; Shockravi A. Tetrahedron Lett. 2005, 46(20),
.76(dd, 1H, ArH), 9.35(s, 1H, olefinic CH), ); IR, ꢀ (KBr disc):
-1
+
230, 1675 cm , EIMS (70ev) m/z: (M 221), Anal. Calcd. for
C H NO : C, 76.01%; H, 3.16%; N, 6.33%; found C, 75.61%;
H, 3.08%; N, 6.21%.
14
7
2
[
[
1
2
d: HNMR ꢁ (CDCl ): 4.15(s, 3H, OMe), 6.99(d, 1H, ArH),
3
3501; [b] Valizadeh H.; Shockravi A. J. Heterocyclic Chem. 2006,
43, 1; [c] Valizadeh H.; Mamaghani M.; Badrian A. Synth. Commun.
2005, 35(6) 785; [d] Valizadeh H.; Shockravi A. Heterocyclic
Commun. 2004, 10(5) 475 [e] Shockravi A.; Sharghi H.; Valizadeh
H.; Heravi M. M. Indian J. Heterocyclic Chem. 2002, 11, 331; [f]
Shockravi A.; Valizadeh H.; Heravi M. M.; Ghadim H. A. J. Chem.
Research (s), 2003, 718.
7
7
.30(m, 1H, ArH), 7.39(m, 1H, ArH), 7.59(d, 1H, ArH),
.62(dd, 1H, ArH), 7.72(dd, 1H, ArH), 8.98(s,1H,olefinic CH),
-1
+
IR, ꢀ (KBr disc): 1735, 1685 cm , EIMS (70ev) m/z: (M 283,
Anal. Calcd. for C H O : C, 70.86%; H, 3.93%; found C,
6
1
5
10
4
9.90%; H, 3.90%.
Acknowledgement. The office of the Research Vice
Chancellor of Azarbaijan University of Tarbiat Moallem
provided support for this work.
[25] Shockravi A.; Sharghi H.; Valizadeh H.; Heravi M. M.
Phosphorus, Sulfur, and Silicon and the related Elements, 2002,
177(11), 2555.