1918
SURESH, D. KUMAR, AND J. S. SANDHU
(d), 129.6 (d), 118.8 (d), 52.2 (q); IR (KBr) 1710, 1635, 1006, 82 cmꢁ1; MS m=z
196 (Mþ).
Compound 3d. 1H NMR (CDCl3) d 7.67 (d, J ¼ 16.0 Hz, 1H), 7.42
(d, J ¼ 8.1 Hz, 2H), 7.19 (d, J ¼ 8.0 Hz, 2H), 6.40 (d, J ¼ 16.0 Hz, 1H), 3.80 (s,
3H), 2.37 (s, 3H); 13C NMR (CDCl3) d 167.6 (s), 144.9 (d), 140.7 (s), 130.7 (s),
129.6 (d), 128.1 (d), 116.7 (d), 51.6 (q), 21.5 (q); IR (KBr) 1712, 1634, 818 cmꢁ1
MS m=z 176 (Mþ).
;
ACKNOWLEDGMENTS
The authors are thankful to the Council of Scientific and Industrial Research,
New Delhi, India, for financial assistance and to the Indian National Science
Academy, New Delhi, India, for additional financial support for this research
project.
REFERENCES
1. Thoemel, F.; Hoffmann, W.; Degner, D. Use of etherified p-hydroxycinnamic acid esters
as sunscreens. Eur. Pat. Appl. EP 44,976, February 3, 1982.
2. Gou, D.-M.; Liu, Y.-C.; Chen, C.-S. A practical chemoenzymic synthesis of the taxol C-13
side chain N-benzoyl-(2R,3S)-3-phenylisoserine. J. Org. Chem. 1993, 58, 1287.
3. Koo, J.; Fish, M. S.; Walker, G. N.; Blake, 2,3-Dimethoxycinnamic acid. J. Org. Synth.
Coll. 1963, 4, 327.
4. (a) Jackson, J. G.; Kenner, J. The reactivity of the double bond in coumarins and related
ab-unsaturated carbonyl compounds, part I: Addition of cyanoacetamide to coumarins. J.
Chem. Soc. 1928, 166; (b) Walling, C.; Walfstirm, K. Derivatives of piperazine, XXI:
Synthesis of piperazine and C-substituted piperazines. J. Am. Chem. Soc. 1947, 69, 854.
5. Claisen, L. Zur Darstellung der zimmtsa¨ure und ihrer homologen. Chem. Ber. 1890, 23,
976; (b) Marvel, C. S.; King, W. O. Ethyl cinnamate. Org. Synth. Coll. 1941, 1, 252.
6. Johnson, A. L. Synthesis of the three isomeric ortho-substituted phenylthienyl benzoic
acids. J. Org. Chem. 1976, 41, 1320.
7. Patil, V. J.; Mavers, U. Wittig reactions in the presence of silica gel. Tetrahedron Lett.
1996, 37, 1281; (b) Schiemenz, G. P.; Thobe, J. Aromatische phosphine mit substituenten
zweiter ordnung, III: Eine neue variante der Wittig-Reaktion. Chem. Ber. 1966, 99, 2663.
8. Gruber, A. S.; Pozebon, D.; Monteiro, A. L.; Dupont, J. On the use of phosphine-free
PdCl2(SEt2)2 complex as catalyst precursor for the Heck reaction. Tetrahedron Lett.
2001, 42, 7345.
9. (a) Baruah, B.; Prajapati, D.; Baruah, A.; Sandhu, J. S. BiCl3=CdCl3-catalysed Michael
addition of 1,3-dicarbonyl compounds under microwave irradiations. Tetrahedron
Lett. 1997, 38, 1449; (b) Borah, H. N.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C.
Bismuth(III)chloride–zinc–promoted selective reduction of aromatic nitro compounds
to azoxy compounds. Tetrahedron Lett. 1994, 35, 3167; (c) Boruah, A.; Baruah, B.;
Prajapati, D.; Sandhu, J. S. Biþ3-catalysed regeneration of carbonyl compounds from
hydrazones under microwave irradiations. Synlett 1997, 1251; (d) Thakur, A. J.; Boruah,
A.; Prajapati, D.; Sandhu, J. S. Microwave-induced bismuth trichloride–catalysed
Beckmann rearrangement of oximes. Synth. Commun. 2000, 30, 2105; (e) Wada, M.; Ohki,
H.; Akiba, K. Y. A Grignard-type addition of allyl unit to aldehydes by using bismuth
and bismuth salt. Bull. Chem. Soc. Jpn. 1990, 63, 1738; (f) Suzuki, H.; Ikegami, T.;