5
1
1
White Solid; Yield (93%, 259 mg); H NMR (500 MHz,
White Solid; Yield (70%, 198 mg); H NMR (500 MHz,
ACCEPTED MANUSCRIPT
CDCl3) δ: 7.84 (d, J = 8.5 Hz, 4H), 6.94 (d, J = 8.5 Hz, 4H),
3.81; 13C NMR (126 MHz, CDCl3) δ: 163.2, 134.0, 129.6, 114.5,
55.7.
CDCl3) δ: 8.56 (s, 1H), 7.98–7.83 (m, 6H), 7.64–7.58 (m, 2H),
7.30 (d, J = 8.0 Hz, 2H), 2.38 (s, 3H); 13C NMR (126 MHz,
CDCl3) δ: 144.3, 138.9, 138.8, 135.1, 132.4, 130.1, 129.7, 129.5,
129.2, 129.0, 128.0, 127.9, 127.7, 122.8, 21.7.
5.15. 1,2-Dimethoxy-4-tosylbenzene (3o)12c
:
5.24. 1-Methyl-4-(octylsulfonyl)benzene (3x)33:
1
White Solid; Yield (94%, 275 mg); H NMR (500 MHz,
CDCl3) δ: 7.81 (d, J = 8.5 Hz, 2H), 7.56 (d, J = 8.5 Hz, 1H), 7.38
(s, 1H), 7.29 (d, J = 8.0 Hz, 2H), 6.93 (d, J = 8.5 Hz, 1H), 3.91
(s, 6H), 2.39 (s, 3H); 13C NMR (126 MHz, CDCl3) δ: 153.0,
149.3, 144.0, 139.4, 133.6, 123.0, 127.4, 121.8, 111.0, 110.0,
56.3, 56.2, 21.6.
1
Colorless oil; Yield (75%, 201 mg); H NMR (500 MHz,
CDCl3) δ: 7.79 (d, J = 8.5 Hz, 2H), 7.36 (d, J = 8.0 Hz, 2H), 3.08
(t, J = 8.5 Hz, 2H), 2.44 (s, 3H), 1.72–1.66 (m, 2H), 1.35–1.22
(m, 10H), 0.87 (t, J = 8.0 Hz, 3H); 13C NMR (126 MHz, CDCl3)
δ: 144.6, 136.2, 129.9, 128.0, 56.4, 31.6, 28.9, 28.9, 28.2, 22.7,
22.6, 21.6, 14.0.
5.16. 1-(tert-Butyl)-4-((4-methoxyphenyl)sulfonyl)benzene (3p):
5.25. 2-(Phenylsulfonyl)thiophene (3y)34:
1
White Solid; Yield (91%, 277 mg); H NMR (500 MHz,
1
CDCl3) δ: 7.89–7.87 (m, 2H), 7.84–7.81 (m, 2H), 7.49–7.47 (m,
2H), 6.97–6.94 (m, 2H), 3.83 (s, 3H), 1.30 (s, 9H); 13C NMR
(126 MHz, CDCl3) δ: 163.4, 156.8, 139.5, 133.7, 129.9, 127.3,
126.3, 114.6, 55.7, 35.3, 31.2. HRMS: calcd. For C17H21O3S
(M+H)+: 305.1206; Found: 305.1181.
White Solid; Yield (82%, 184 mg); H NMR (500 MHz,
CDCl3) δ: 8.00 (d, J = 8.0 Hz, 2H), 7.70 (d, J = 4.0 Hz, 1H), 7.65
(d, J = 4.5 Hz, 1H), 7.59–7.50 (m, 3H), 7.09 (t, J = 4.5 Hz, 1H);
13C NMR (126 MHz, CDCl3) δ: 143.1, 142.1, 134.0, 133.5,
133.4, 129.4, 127.9, 127.7, 127.4.
5.17. 1-Methoxy-4-(phenylsulfonyl)benzene (3q)27:
5.26. 2-Tosylthiophene (3z)35:
1
1
White Solid; Yield (86%, 214 mg); H NMR (500 MHz,
White Solid; Yield (87%, 207 mg); H NMR (500 MHz,
CDCl3) δ: 7.91–7.86 (m, 4H), 7.52–7.45 (m, 3H), 6.96 (d, J = 8.5
Hz, 2H), 3.82 (s, 3H); 13C NMR (126 MHz, CDCl3) δ: 163.5,
142.4, 133.1, 132.9, 129.9, 129.3, 127.4, 114.6, 55.7.
5.18. 1-Methoxy-4-tosylbenzene (3r)31:
CDCl3) δ: 7.88 (d, J = 8.0 Hz, 2H), 7.67 (d, J = 3.0 Hz, 1H), 7.62
(d, J = 4.5 Hz, 1H), 7.32 (d, J = 7.5 Hz, 2H), 7.07 (t, J = 4.0 Hz,
1H), 2.41 (s, 3H); 13C NMR (126 MHz, CDCl3) δ: 144.5, 143.6,
139.3, 133.7, 133.2, 130.1, 127.9, 127.5, 21.7.
1
Acknowledgements
White Solid; Yield (89%, 233 mg); H NMR (500 MHz,
CDCl3) δ: 7.87 (d, J = 9.0 Hz, 2H), 7.80 (d, J = 8.5 Hz, 2H), 7.28
(d, J = 8.5 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 3.83 (s, 3H), 2.38
(s, 3H); 13C NMR (126 MHz, CDCl3) δ: 163.3, 143.9, 139.6,
133.7, 130.0, 129.8, 127.5, 114.6, 55.7, 21.6.
We are thankful to CSIR, New Delhi for financial support
(File No. 02/(0285)/16/EMR-II). AKP is thankful to DST, New
Delhi for INSPIRE fellowship and SK is thankful to CSIR, New
Delhi for SRF.
5.19. 1-(tert-Butyl)-4-(phenylsulfonyl)benzene (3s)32:
Supplementary data
1
White Solid; Yield (83%, 228 mg); H NMR (500 MHz,
Supplementary data associated with this article can be found
in the online version at
CDCl3) δ: 7.96–7.94 (m, 2H), 7.87 (d, J = 8.5 Hz, 2H), 7.55–7.48
(m, 5H), 1.30 (s, 9H); 13C NMR (126 MHz, CDCl3) δ: 157.2,
142.1, 138.7, 133.1, 129.3, 127.6, 127.7, 126.4, 35.3, 31.2.
5.20. 1-Methoxy-3-tosylbenzene (3t)27:
References and notes
1. (a) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X.
Chem. Soc. Rev. 2015, 44, 291; (b) Chauhan, P.; Mahajan, S.;
Enders, D. Chem. Rev. 2014, 114, 8807; (c) Wang, L.; Hea, W.;
Yu, Z. Chem. Soc. Rev. 2013, 42, 599; (d) Kondo, T.; Mitsudo, T.-
a. Chem. Rev. 2000, 100, 3205.
1
White Solid; Yield (69%, 181 mg); H NMR (500 MHz,
CDCl3) δ: 7.83 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 7.5 Hz, 1H), 7.44
(s, 1H), 7.40 (t, J = 8.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.07 (d,
J = 8.0 Hz, 1H), 3.83 (s, 3H), 2.39 (s, 3H); 13C NMR (126 MHz,
CDCl3) δ: 160.1, 144.3, 143.2, 138.7, 130.4, 130.0, 127.8, 119.9,
119.5, 112.2, 55.8, 21.7.
2. Parent, E. E.; Dence, C. S.; Jenks, C.; Sharp, T. L.; Welch, M. J.;
Katzenellenbogen, J. A. J. Med. Chem. 2007, 50, 1028.
3. Crosignani, S.; Pretre, A.; Lebrun, C. J.; Fraboulet, G.; Seenisamy,
J.; Augustine, J. K.; Missotten, M.; Humbert, Y.; Cleva, C.; Abla,
N.; Aaff, H.; Schott, O.; Schneider, M.; Charvillon, F. B.; Rivron,
D.; Namernig, I.; Arrighi, J. F.; Gaudet, M.; Zimmerli, S. C.;
Juillard, P.; Joson, Z. J. Med. Chem. 2011, 54, 7299.
4. Hussain, I.; Yawer, M. A.; Lalk, M.; Lindequist, U.; Villinger, A.;
Fischer, C.; Langer, P. Bioorg. Med. Chem. 2008, 16, 9898.
5. (a) Xu, W.; He, J.; He, M.; Han, F.; Chen, X.; Pan, Z.; Wang, J.;
Tong, M. Molecules 2011, 16, 9129; (b) Otzen, T.; Wempe, E. G.;
Kunz, B.; Bartels, R.; Yvetot, G. L.; Hansel, W.; Schaper, K. J.;
Seydel, J. K. J. Med. Chem. 2004, 47, 240.
5.21. 1-(tert-Butyl)-4-tosylbenzene (3u)30:
1
White Solid; Yield (85%, 245 mg); H NMR (500 MHz,
CDCl3) δ: 7.83–7.81 (m, 4H), 7.49–7.46 (m, 2H), 7.28 (d, J = 8.0
Hz, 2H), 2.37 (s, 3H), 1.28 (s, 9H); 13C NMR (126 MHz, CDCl3)
δ: 157.0, 144.0, 139.1, 130.0, 127.8, 127.5, 126.4, 35.3, 31.2,
21.7.
5.22. 1,3,5-Trimethyl-2-(phenylsulfonyl)benzene (3v)27:
6. (a) Prasit, P.; Wang, Z.; Brideau, C.; Chan, C.-C.; Charleson, S.;
Cromlish, W.; Ethier, D.; Evans, J. F.; Hutchinson, A. W. F.;
Gauthier, J. Y.; Gordon, R.; Guay, J.; Gresser, M.; Kargman, S.;
Kennedy, B.; Leblanc, Y.; L´eger, S.; Mancini, J.; O'Neill, G. P.;
Ouellet, M.; Percival, M. D.; Perrier, H.; Riendeau, D.; Rodger, I.;
Tagari, P.; Th´erien, M.; Vockers, P.; Wong, E.; Xu, L. J.; Young,
R. N.; Zamboni, R.; Boyce, S.; Rupniak, N.; Forrest, M.; Visco,
D.; Patrick, D. Bioorg. Med. Chem. Lett. 1999, 9, 1773; (b)
Hawkey, C. J. Lancet 1999, 353, 307.
Yellow oil; Yield (69%, 180 mg); 1H NMR (500 MHz,
CDCl3) δ: 7.80–7.78 (m, 2H), 7.56–7.53 (m, 1H), 7.49–7.46 (m,
2H), 6.95 (s, 2H), 2.60 (s, 6H), 2.30 (s, 3H); 13C NMR (126
MHz, CDCl3) δ: 143.7, 143.5, 140.3, 133.9, 132.7, 132.3, 129.0,
126.4, 23.0, 21.2.
5.23. 2-Tosylnaphthalene (3w)29:
7. Regina, G. L.; Coluccia, A.; Brancale, A.; Piscitelli, F.; Famiglini,
V.; Cosconati, S.; Maga, G.; Samuele, A.; Gonzalez, E.; Clotet,