514
B. T. S. Thirumamagal, S. Narayanasamy / Tetrahedron Letters 49 (2008) 512–515
21. Birsen, T.; Esra, K.; Erdem, Y.; Mevluet, E. Bioorg. Med. Chem.
2007, 15, 1808.
22. De Martino, G.; La Regina, G.; Ragno, R.; Coluccia, A.; Bergamini,
A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.;
Silvestri, R. Antiviral Chem. Chemother. 2006, 17, 59.
23. Narayanasamy, S.; Thirumamagal, B. T. S.; Johnsamuel, J.; Byun, Y.;
Al-Madhoun, A. S.; Usova, E.; Cosquer, G. Y.; Yan, J.; Bandyo-
padhyaya, A. K.; Tiwari, R.; Eriksson, S.; Tjarks, W. Bioorg. Med.
Chem. 2006, 14, 6886.
24. Byun, Y.; Thirumamagal, B. T. S.; Yang, W.; Eriksson, S.; Barth, R.
F.; Tjarks, W. J. Med. Chem. 2006, 49, 5513.
under conventional and microwave conditions. Both the
percent yield and the reaction duration were considerably
improved under microwave irradiation (Scheme 1).
Though it was perceived that methyl-o-[a-phenylsulfo-
nyl]toluate 1 could lead to the vinylsulfones with substi-
tuted benzaldehydes, our present study has demonstrated
a novel mode of condensation of 4-bromobenzaldehye
and dichlorobenzaldehydes with sulfone leading to the
formation of 2-arylindanediones which have attracted con-
siderable interest due to their anticoagulant and parasiti-
25. Thirumamagal, B. T. S.; Zhao, X. B.; Bandyopadhyaya, A. K.;
Narayanasamy, S.; Johnsamuel, J.; Tiwari, R.; Golightly, D. W.;
Patel, V.; Jehning, B. T.; Backer, M. V.; Barth, R. F.; Lee, R. J.;
Backer, J. M.; Tjarks, W. Bioconjugate Chem. 2006, 17, 1141.
26. Thirumamagal, B. T. S.; Cosquer, J.; Johnsamuel, G. Y.; Byun, Y.;
Yan, J.; Narayanasamy, S.; Tjarks, W.; Barth, R. F.; Al-Madhoun,
A. S.; Eriksson, S. Nucleosides Nucleotides Nucl. 2006, 25, 861.
27. Xian, H.; Jian, X. J. Org. Chem. 2007, 72, 3965.
cidal activities.
A new and previously unreported
approach to 3-alkylatedphthalide under microwave and
conventional heating has also been presented.
Acknowledgements
28. 2-(20,60-Dichlorophenyl)indane-1,3-dione (2a): mp 154–156 °C (lit.29
BTST acknowledges UGC-SAP for instrument grants to
the department and University of Madras for a URF. The
authors thank Professor Velmurugan, Biophysics and
Crystallography Department, University of Madras for
X-ray diffraction studies of some of the compounds. The
authors also thank Mr. Brian R Crouse for his help.
158 °C); IR (KBr) 750, 1725, 1760, 3400 cmꢀ1 1H NMR (CDCl3) d
;
8.1 (s, 2H), 7.9 (s, 2H), 7.4 (s, 2H), 7.1 (s, 1H), 5.2 (s, 1H); 13C NMR
(CDCl3) d 196.0, 141.3, 138.1, 135.7, 130.0, 128.4, 128.3, 123.5, 59.1;
exact mass (HR EI) calcd for C15H8Cl2O2: m/z 289.9956; found, m/z
289.7280, with isotopic clusters at 291.8120 and 293.8010; 2-(20,40-
Dichlorophenyl)indane-1,3-dione (2b): mp 141–143 °C (lit.29 143–
145 °C); IR (KBr) 750, 1300, 1450, 1729, 1740, 3259 cmꢀ1 1H
;
NMR (CDCl3) d 7.9 (s, 1H), 7.8–7.6 (m, 5H), 6.5 (s, 1H), 5.19 (s, 1H);
13C NMR (CDCl3) d 197.0, 138.0, 137.5, 136.5, 133.8, 132.7, 130.4,
129.6, 128.5, 126.9, 61.9; exact mass (EI) calcd for C15H8Cl2O2: m/z
289.9956; found, m/z 289.7278 with isotopic clusters at 291.8958 and
293.8010; 2-(40-Bromophenyl)indane-1,3-dione (2d): mp 141–143 °C
References and notes
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(lit.29 142–146 °C); IR (KBr) 700, 1300, 1456, 1735, 1744, 3245 cmꢀ1
;
1H NMR (CDCl3) d 7.9–7.4 (m, 8H), 5.3 (s, 1H); 13C NMR (CDCl3) d
194.5, 137.5, 136.6, 132.8, 132.2, 129.7, 128.9, 122.5, 68.4; exact mass
(EI) calcd for C15H9BrO2: m/z 299.9826; found, m/z 299.9237 with
isotopic cluster at 301.9440.
29. (a) Horton, R. L.; Murdock, K. C. J. Org. Chem. 1960, 25, 938; (b)
Shapiro, L.; Geiger, K.; Freedman, L. J. Org. Chem. 1960, 25, 1860.
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30. Mp 180–182 °C; IR (KBr) 750, 1398, 1548, 1716 cmꢀ1 1H NMR
;
(CDCl3) d 8.1–7.1 (m, 12H), 3.8 (s, 3H); 13C NMR (CDCl3) d 165.7,
139.1, 139.4, 138.5, 138.47, 137.2, 135.8, 135.3, 133.4, 130.8, 129.5,
129.1, 126.8, 126.4, 126.0, 125.4, 123.5, 52.0; Anal. Calcd for
C
22H15Cl2NO6S: C, 53.67, H, 3.07. Found: C, 53.52, H, 3.13.
7. Ryuhei, N.; Pavel, A., Jr. Org. Lett. 2006, 8, 359.
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Tetrahedron Lett. 2001, 42, 1647; (b) Toga, H.; Muraki, T.; Yoshina,
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32. o-[a-Phenylsulfonyl]ethylbenzoic acid (4a): mp 180–182 °C; IR (KBr)
761, 1442, 1579, 1706, 2987 cmꢀ1 1H NMR (CDCl3) d 7.9–7.2 (m,
;
11H), 6.1 (q, 1H), 2.2 (d, J = 8.2 Hz, 3H); 13C NMR (CDCl3) d 171.4,
138.5, 137.1, 135.4, 133.6, 132.9, 131.4, 129.8, 129.5, 128.7, 128.5,
58.8, 14.2; Anal. Calcd for C15H14O4S: C, 62.05, H, 4.86; Found: C,
62.15, H, 4.63. o-[a-Phenylsulfonyl-n-propyl]benzoic acid (4b): mp
178–180 °C; IR (KBr) 759, 1388, 1411, 2925 cmꢀ1; 1H NMR (CDCl3)
d 8.0–7.1 (m, 10H), 6.0 (t, J = 7.8 Hz, 1H), 2.4 (m, 2H), 0.98 (t,
J = 7.4 Hz, 3H); 13C NMR (CDCl3) d 171.4, 137.2, 133.8, 133.2,
132.7. 131.3, 130.2, 129.1, 128.5, 128.3, 128.3, 64.9, 29.3, 10.8. Anal.
Calcd for C16H16O4S: C, 63.14, H, 5.30. Found: C, 63.29, H, 5.21.
o-[a-Phenylsulfonyl-b-phenethyl]benzoic acid (4c): mp 140–142 °C. IR
(KBr) 760, 1380, 676, 2920 cmꢀ1 1H NMR (CDCl3) d 8.7–7.5 (m,
;
15H), 6.1 (t, J = 8.2 Hz, 1H), 4.9 (m, 2H); 13C NMR (CDCl3) d 172.8,
138.5, 138.4, 137.2, 133.8, 133.5, 131.5, 129.8, 129.5, 128.2, 128.8,
127.5, 127.9, 126.5, 125.47, 64.1, 29.6; Anal. Calcd for C21H18O4S: C,
68.83, H, 4.95. Found: C, 68.79, H, 4.89.
33. 3-Methylphthalide (5a): IR (KBr) 760, 1730 cmꢀ1; H NMR (CDCl3)
1
d 7.8–6.9 (m, 4H), 5.5 (q, J = 9.1 Hz, 1H), 1.6 (d, J = 9.1 Hz, 3H); 13
C
NMR (CDCl3) d 170.4, 151.1, 134.0, 129.0, 129.0, 125.7, 125.7, 75.3,
20.3; exact mass (EI) calcd for C9H8O2: m/z 148.0517; found, m/z
20. Frankel, B. A.; Bentley, M.; Kruger, R. G.; McCafferty, D. G. J. Am.
Chem. Soc. 2004, 126, 3404.