J 7.6), 7.22 (4H, d + t J 7.5), 7.20 (1H, t, J 7.6), 7.10 (1H, t, J 7.5),
6.04 (1H, d, J 1.6), 3.95 (1H, dd, J 15.7, 1.6), 3.81 (1H, d, 15.7); m/z
(EI) 259 (M + 4), 257 (M + 2), 255 (M+).
Acknowledgements
We thank the Centro di Metodologie Chimico-Fisiche and the
Centro Interdipartimentale di Metodologie Chimico-Fisiche of the
University of Naples “Federico II” for the instrumental support.
This work was supported by a grant of the Ministero dell’Università
e della Ricerca Scientifica e Tecnologica (Roma).
2,3-di-p-tolyl-1,3-thiazolidin-4-one (3b)
White solid; mp 119–20 °C (Found: C, 72.15; H, 6.00; N, 4.93.
Calc. for C17H17NOS: C, 72.05; H, 6.05; N, 4.94%); H (C6D6) 7.18
(2H, d, J 7.6), 7.08 (2H, d, J 7.5), 7.06 (2H, d, J 7.6), 7.02 (2H, d,
J 7.5), 6.01 (1H, d, J 1.7), 3.98 (1H, dd, J 15.7, 1.7), 3.87 (1H, d, J
15.7), 2.26 (3H, s), 2.22 (3H, s); m/z (EI) 287 (M + 4), 285 (M + 2),
283 (M+).
References
1 M. V. Diurno, G. Greco, O. Mazzoni, E. Novellino,A. Calignano, G. La
Rana, A. Barbieri and A. Bolognese, Med. Chem. Res., 1994, 4, 578.
2 A. Bolognese, M. V. Diurno, G. Greco, P. Grieco, O. Mazzoni,
E. Novellino, E. Perissutti and C. Silipo, J. Recept. Res., 1995, 15, 631.
3 M. V. Diurno, O. Mazzoni, G. Correale, I. Gomez Monterrey,
A. Calignano, G. La Rana and A. Bolognese, Farmaco, 1999, 54, 579.
4 M. V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano and
A. Bolognese, J. Med. Chem., 1992, 32, 2910.
5 A. Bolognese, M. V. Diurno, O. Mazzoni, G. Correale, I. Gomez
Monterrey and V. Barone, J. Mol. Graph. Model., 1999, 54, 579.
6 (a) S. Caddick, Tetrahedron, 1995, 51, 10403; (b) S. A. Galema,
Chem. Soc. Rev., 1997, 26, 233; (c) R. S. Varma, Green Chem., 1999,
1, 43; (d) A. Loupy and L. Perreux, Tetrahedron, 2001, 57, 9199;
(e) P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron,
2001, 57, 25; (f) M. Larhed and A. Hallberg, DDT, 2001, 6, 406;
(g) A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH, Weinheim,
2002.
2-p-tolyl-3-phenyl-1,3-thiazolidin-4-one (3c)
White solid; mp 106–7 °C (Found: C, 71.38; H, 5.60; N, 5.19. Calc.
for C16H15NOS: C, 71.34; H, 5.61; N, 5.20%); H (C6D6) 7.31 (1H, t,
J 7.5), 7.27 (2H, d, J 7.5), 7.19 (4H, d + t, J 7.6), 7.10 (2H, d, J 7.5),
6.07 (1H, d, J 1.5), 3.99 (1H, dd, J 15.8, 1.5), 3.87 (1H, d, 15.8), 2.28
(3H, s); m/z (EI) 273 (M + 4), 271 (M + 2), 269 (M+).
2-phenyl-3-p-tolyl-1,3-thiazolidin-4-one (3d)
White solid; mp 115–7 °C (Found: C, 71.30; H, 5.59; N, 5.20. Calc.
for C16H15NOS: C, 71.34; H, 5.61; N, 5.20%); H (C6D6) 7.30 (1H,
t, J 7.4), 7.29 (2H, d, J 7.4), 7.27 (2H, t, J 7.4), 7.14 (2H, d, J 8.4),
7.12 (2H, d, J 8.4), 6.06 (1H, d, J 1.5), 4.03 (1H, dd, J 15.8, 1.5),
3.90 (1H, d, 15.8), 2.21 (3H, s); m/z (EI) 273 (M + 4), 271 (M + 2),
269 (M+).
7 (a) M. V. Diurno, O. Mazzoni, E. Piscopo and A. Bolognese, Farmaco,
1992, 47, 239; (b) A. Bolognese, M. V. Diurno, O. Mazzoni and
F. Giordano, Tetrahedron, 1991, 47, 7417.
8 Y. Allingham, R. C. Cookson and T. A. Crabb, Tetrahedron, 1968, 24,
1989.
9 J. Tierney, J. Heterocyclic Chem., 1989, 26, 997.
10 A. R. Surrey, J. Am. Chem. Soc., 1947, 69, 2911.
2-p-chlorophenyl-3-phenyl-1,3-thiazolidin-4-one (3e)
11 G. W. Stacy and R. Morath, J. Am. Chem. Soc., 1952, 74, 3885.
12 V. Barone, O. Crescenzi and R. Improta, Quant. Struct. Act. Relat.,
2002, 21, 105.
13 E. Langella, E. Rege, R. Improta, O. Crescenzi and V. Barone, J.
Comput. Chem., 2002, 23, 650.
14 C. Adamo and V. Barone, J. Chem. Phys., 1999, 110, 6158.
15 J. B. Collins, P. R. Schleyer, J. S. Binkley and J. A. Pople, J. Chem.
Phys., 1976, 64, 5142.
White solid; mp 129–30 °C (Found: C, 62.20; H, 4.18; N, 4.84.
Calc. for C15H12ClNOS: C, 62.17; H, 4.17; N, 4.83%); H (C6D6)
7.30 (1H, t, J 7.5), 7.29 (4H, d + t, J 7.6), 7.25 (2H, d, J 7.5), 7.14
(2H, d, J 7.5), 6.10 (1H, d, J 1.6), 4.01 (1H, dd, J 15.8, 1.6), 3.89
(1H, d, 15.8); m/z (EI) 293 (M + 4), 291 (M + 2), 290 (M + 1),
289 (M+).
16 J. R. Cheeseman, G. W. Trucks, T. A. Keith and M. J. Frisch, J. Chem.
Phys., 1998, 104, 5497.
2-phenyl-3-p-chlorophenyl-1,3-thiazolidin-4-one (3f)
17 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C.
Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci,
M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji,
M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida,
T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox,
H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts,
R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli,
J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador,
J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C.
Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B.
Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski,
B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi,
R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng,
A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen,
M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian 03, Gaussian, Inc.,
Pittsburgh, 2003.
White solid; mp 110–1 °C (Found: C, 62.23; H, 4.16; N, 4.84. Calc.
for C15H12ClNOS: C, 62.17; H, 4.17; N, 4.83%); H (C6D6) 7.22 (5H,
m), 7.20 (2H, d, J 7.6), 7.07 (2H, d, J 7.6), 6.03 (1H, d, J 1.6), 3.94
(1H, dd, J 15.8, 1.6), 3.84 (1H, d, 15.8); m/z (EI) 293 (M + 4), 291
(M + 2), 290 (M + 1), 289 (M+).
2-p-nitrophenyl-3-phenyl-1,3-thiazolidin-4-one (3g)
White solid; mp 133–4 °C (Found: C, 59.98; H, 4.05; N, 9.32. Calc.
for C15H12N2O3S: C, 59.99; H, 4.03; N, 9.33%); H (C6D6) 8.14 (2H,
d, J 7.1), 7.47 (2H, d, J 7.1), 7.30 (2H, t, J 7.5), 7.19 (3H, d + t, J
7.5), 6.20 (1H, d, J 1.6), 4.01 (1H, dd, J 15.8, 1.6), 3.90 (1H, d,
15.8); m/z (EI) 304 (M + 4), 302 (M + 2), 300 (M+).
2-phenyl-3-p-nitrophenyl-1,3-thiazolidin-4-one (3h)
18 S. Higashiya, S. Narizuka, A. Konno, T. Maeda, K. Momota and
T. Fuchigami, J. Org. Chem., 1999, 64, 133.
White solid; mp 102–3 °C (Found: C, 59.97; H, 4.05; N, 9.32. Calc.
for C15H12N2O3S: C, 59.99; H, 4.03; N, 9.33%); H (C6D6) 7.99
(2H, t, J 7.5), 7.28 (2H, t, J 7.6), 7.26 (2H, d, J 7.5), 7.21 (1H, t,
J 7.5), 6.56 (2H, d, J 7.5), 6.18 (1H, d, J 1.6), 3.94 (1H, dd, J 15.8,
1.6), 3.83 (1H, d, 15.8); m/z (EI) 293 (M + 4), 291 (M + 2), 290
(M + 1), 289 (M+).
19 (a) I. Fleming, Frontier Orbitals and Organic Chemical Reactions;
John Wiley & Sons, Chichester, U.K., 1976; (b) R. Breslow, Organic
Reaction Mechanisms, W. A. Benjamin, Inc, New York, 1965.
20 (a) C. Reichardt, Solvents and Solvent Effect in Organic Chemistry,
VCH Publishers, Weinheim, 2nd edn., 1988; (b) A. J. Parker, Chem.
Rev., 1969, 69, 1.
O r g . B i o m o l . C h e m . , 2 0 0 4 , 2 , 2 8 0 9 – 2 8 1 3
2 8 1 3