S. Mallouk et al. / Tetrahedron Letters 45 (2004) 4143–4148
4147
8a: IR (KBr) 1735, 1685, 1559, 1531, 1529, 1523 cmꢁ1
.
Woodnutt, D. J.. Tetrahedron Lett. 1984, 25, 977; (i)
Schultz, A. G.; Ravichandran, R.. Tetrahedron Lett. 1981,
22, 1771.
1H NMR (CDCl3): d 8.01–7.29 (19H, m). 13C NMR
(CDCl3): d 200.01, 149.05, 148.56, 140.01, 139.99,
134.88, 133.33, 130.35, 129.99, 129.89, 129.89, 129.87,
129.68, 128.98, 128.01, 127.86, 127.68, 125.00, 119.18,
118.23. CIMS (isobutane, reagent gas): m=z 435
[M þ H]þ. Data for 8b: IR (KBr) 1735, 1685, 1559, 1531,
2. Gilchrist, T. L. Heterocyclic Chemistry. 3rd ed.; Addison-
Wesley Longman: England, 1998; Lednicer, D. Strategies
for Organic Drugs Synthesis and Design; Wiley & Sons:
New York, 1998. Chapters 8 and 9.
3. (a) Huisgen, R.; Seidel, M.; Wallbillich, G.; Knupfer, H.
Tetrahedron 1962, 17, 3; (b) Padmavathi, V.; Reddy, A. V.
B.; Sumathi, R. P.; Padmaja, A.; Reddy, D. B. Indian J.
Chem., Sect. B 1998, 37, 1286; (c) Walker, D.; Hiebert, J.
D. Chem. Rev. 1967, 67, 153; (d) Le Qhoc, K.; Laude, B.
C.R. Acad. Sci. 1973, 276, 109; (e) Streith, J.; Kiehl, G.;
Fritz, H. Tetrahedron Lett. 1974, 15, 631; (f) Halton, D.
D.; Morrisson, G. A. J. Chem. Res. (S) 1979, 332; (g)
Franck-Neumann, M.; Miesch, M. Tetrahedron Lett.
1982, 23, 1409; (h) Bhatnagar, I.; George, M. V. Tetra-
hedron 1968, 24, 1293; (i) Auwers, K.; Heimke, P. Liebigs
Ann. 1927, 458, 186; (j) Smith, L. I.; Howard, K. L. J. Am.
Chem. Soc. 1943, 65, 159; (k) Singh, S. P.; Kumar, D.;
Prakash, O.; Kapoor, R. P. Synth. Commun. 1997, 27,
2683; (l) Dodwadmath, R. P.; Wheeler, T. S. Proc. Ind.
Acad. Sci. 1935, 2A, 438; (m) Nakamishi, N.; Kawashita,
Y.; Hayashi, M. Org. Lett. 2002, 4, 3955.
1
1529, 1523 cmꢁ1. H NMR (CDCl3): d 8.01–7.29 (19H,
m). 13C NMR (CDCl3): d 200.01, 148.56, 140.01, 139.99,
137.62, 136.43, 134.88, 133.33, 130.35, 129.99, 129.89,
129.89, 129.87, 129.68, 128.98, 128.01, 127.86, 127.68,
125.00, 119.18. CIMS (isobutane, reagent gas): m=z 435
[M þ H]þ.
4.1.9. 1,3,5-Triphenyl-4-paramethylbenzoylpyrazole (9a)
and 1,3,4-triphenyl-5-paramethylbenzoylpyrazole (9b).
Mp 132–134 °C (EtOH) (lit.7a 133–134 °C). Data for
9a: IR (KBr) 1660, 1610, 1598, 1576, 1518, 1499 cmꢁ1
.
1H NMR (CDCl3): d 8.16–7.00 (19H, m), 2.41 (3H, s).
13C NMR (CDCl3): d 197.94, 148.15, 145.57, 140.01,
139.95, 132.78, 131.49, 130.38, 129.66, 129.28, 129.21,
128.79, 128.80, 128.71, 128.38, 127.51, 126.88, 124.58,
118.99, 117.26, 21.80. CIMS (isobutane, reagent gas):
m=z 415 [M þ H]þ. Data for 9b: IR (KBr) 1660, 1610,
1598, 1576, 1518, 1499 cmꢁ1. 1H NMR (CDCl3): d 8.16–
7.00 (19H, m), 2.52 (3H, s). 13C NMR (CDCl3): d
197.94, 145.57, 140.01, 139.95, 135.42, 132.78, 131.49,
130.38, 129.66, 129.28, 129.21, 128.79, 128.80, 128.71,
128.38, 127.51, 126.88, 125.66, 124.58, 118.99, 21.90.
CIMS (isobutane, reagent gas): m=z 415 [M þ H]þ.
4. Soufiaoui, M., non published works.
5. (a) Keinan, E.; Mazur, Y. J. Am. Chem. Soc. 1977, 99,
3861 J. Org. Chem. 1978, 43, 1020; (b) Posner, G. H.
Angew. Chem. 1978, 90, 527 Angew. Chem., Int. Ed. Engl.
1978, 17, 48; (c) McKillop, A.; Young, D. W. Synthesis
1979, 401, and 481; (d) Villemin, D.; Ricard, M. Tetra-
hedron Lett. 1984, 25, 1059; (e) Foucaud, A.; Bram, G.;
Loupy, A. In Preparative Chemistry Using Supported
Reagents; Lazslo, P., Ed.; Academic: San Diego, 1987;
p 317, Chapter 17; (f) Smith, K. Solid Supports and
Catalysts in Organic Synthesis; Allis Horwood PTR
€
Prentice Hall, 1992 (g) Lidstrom, P.; Tierney, J.; Wathey,
B.; Westman, J. Tetrahedron. p. 9225; (h) Blass, B. E.
Tetrahedron 2002, 58, 9301.
4.1.10. 1,3,5-Triphenyl-4-paramethoxybenzoylpyrazole
(10a) and 1,3,4-triphenyl-5-paramethoxybenzoyl pyrazole
(10b). Mp 112–114 °C (EtOH) (lit.7a 112–113 °C). Data
for 10a: IR (KBr) 1647, 1600, 1597, 1575, 1521,
1497 cmꢁ1. 1H NMR (CDCl3): d 8.01–6.95 (19H, m), 4.01
(3H, s). 13C NMR (CDCl3): d 199.33, 148.00, 147.25,
140.12, 138.89, 134.55, 132.73, 130.36, 129.82, 129.37,
129.60, 129.67, 129.00, 128.66, 128.56, 127.44, 127.34,
124.67, 119.00, 117.99, 56.13. CIMS (isobutane, reagent
gas): m=z 431 [M þ H]þ. Data for 10b: IR (KBr) 1647,
1600, 1597, 1575, 1521, 1497 cmꢁ1. 1H NMR (CDCl3): d
8.01–6.95 (19H, m), 4.11 (3H, s). 13C NMR (CDCl3): d
199.33, 147.25, 140.12, 138.89, 136.44, 134.55, 132.73,
130.36, 129.82, 129.37, 129.60, 129.67, 129.00, 128.66,
128.56, 127.44, 127.34, 125.02, 124.67, 119.00, 56.33.
CIMS (isobutane, reagent gas): m=z 431 [M+H]þ.
6. (a) Balogh, M.; Cornelis, A.; Laszlo, P. Tetrahedron Lett.
1984, 25, 3313; (b) Cornelis, A.; Laszlo, P. Synthesis 1985,
909; (c) Balogh, M.; Laszlo, P. Organic Chemistry Using
Clays; Springer: Berlin, 1993; (d) Delaude, L.; Laszlo, P. J.
Org. Chem. 1996, 61, 6360.
7. (a) Bougrin, K.; Soufiaoui, M.; El Yazidi, M. Tetrahedron
Lett. 1995, 36, 4065; (b) Varma, R. S.; Saini, R. K.
Tetrahedron Lett. 1997, 38, 2623; (c) Mesheram, H. M.;
Dale, S.; Yadav, J. S. Tetrahedron Lett. 1997, 38, 8743; (d)
Varma, R. S.; Dahiya, R. K. Tetrahedron Lett. 1998, 39,
1307.
8. (a) Einhorn, C.; Einhorn, J.; Luche, J.-L. Sonochemistry-
the use of ultrasonic waves in synthetic organic chemistry.
Synthesis 1988, 787; (b) Ley, S. V.; Low, C. M. R.
Ultrasound in Synthesis; Springer: New York, 1989; (c)
Sonochemistry: The Uses of Ultrasound in Chemistry;
Mason, T. J., Ed.; Royal Society of Chemistry: Cam-
bridge, 1990.
References and notes
9. (a) Ando, T.; Kimura, T. In Advances in Sonochemistry;
Mason, T. J., Ed.; JAI: London, 1991; Vol. 2, pp 211–251;
(b) Davidson, R. In Sonochemistry: The Uses of Ultra-
sound in Chemistry; Mason, T. J., Ed.; The Royal Society
of Chemistry: Cambridge, UK, 1992; p 50; (c) Pestman, J.;
Engberts, J.; Jong, F. Recueil des Travaux Chimiques des
Pays-Bas 1994, 113, 533.
10. (a) Bowser, R.; Davidson, R. In Current Trends in
Sonochemistry; Price, G. J., Ed.; The Royal Society of
Chemistry: Cambridge, UK, 1992; pp 50–58, pp 87–109;
(b) Varma, R. S.; Naicker, K. P. Tetrahedron Lett. 1999,
40, 6177; (c) Luche, J. L. In Grenoble Sciences, Synthetic
Organic Sonochemistry; Plenum: New York, 1998.
1. (a) Parham, W. E.; Dooley, J. F. J. Am. Chem. Soc. 1967,
89, 985; (b) Fusco, R. Pyrazols. In The Chemistry of
Heterocyclic Compounds; Weissberger, A., Ed.; Inter-
science: New York, 1967; 22, pp 1–176; (c) Neuhoeffer,
H.; Cuny, G.; Franke, W. K. Ann 1968, 713, 96; (d)
Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293;
(e) Van Vyve, T.; Viehe, H. G. Angew. Chem., Int. Ed.
Engl. 1973, 12, 806; (f) Hervem, F.; Viehie, H. G. Angew.
Chem., Int. Ed. Engl. 1973, 12, 405; (g) Voghel, G. J.;
Eggeriche, T. L.; Janousek, Z.; Viehie, H. G.. J. Org.
Chem. 1974, 39, 1233; (h) Mackenzie, K.; Proctor, G. J.;