PAPER
S-Arylation of 1,2-Bis(o-amino-1H-pyrazolyl) Disulfides
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HRMS (EI): m/z calcd for C18H935Cl2F3N4O2S (M+): 471.9775;
found: 471.9773.
13C NMR (125 MHz): d = 153.0, 149.2, 140.1, 137.2, 133.6, 132.2,
131.3, 129.8, 127.3, 126.1, 125.9, 124.0, 113.5, 88.8.
LRMS (EI, 70 eV): m/z (%) = 420 (M+ + 2, 15), 419 (22), 418 (M+,
100).
HRMS (EI): m/z calcd for C16H11IN4S (M+): 417.9749; found:
417.9749.
17
White solid; mp 214.1–216.6 °C.
IR (KBr): 3444, 3334, 2243, 1622, 1324, 886 cm–1.
1H NMR (300 MHz): d = 8.09 (s, 2 H), 7.53 (d, J = 5.0 Hz, 1 H),
7.13 (s, 1 H), 7.01 (d, J = 5.0 Hz, 1 H), 6.24 (br s, 2 H).
Diphenylsulfane (23)4i
Colorless oil.
13C NMR (125 MHz): d = 152.4, 136.2, 136.1, 133.7, 133.4, 133.2,
132.5, 131.2, 128.3, 127.5, 127.0, 123.8, 121.6, 121.2, 113.4, 90.3.
1H NMR (300 MHz): d = 7.41–7.30 (m, 10 H).
13C NMR (75 MHz): d = 135.8, 131.0, 129.2, 127.0.
LRMS (EI, 70 eV): m/z (%) = 186 (M+, 100).
LRMS (EI, 70 eV): m/z (%) = 438 (17), 437 (14), 436 (M+ + 2, 73),
435 (20), 434 (M+, 100).
HRMS (EI): m/z calcd for C15H735Cl2F3N4S2 (M+): 433.9441;
found: 433.9441.
Acknowledgment
19
The authors thank the Zhejiang Provincial Natural Science Found-
ation of China (Y407116), National Natural Science Foundation of
China (No 20872112), and Program for New Century Excellent
Talents in University (No. NCET-06-0711) for financial support.
Yellow solid; mp 163.0–164.3 °C.
IR (KBr): 3348, 3338, 2925, 2251, 1626, 1520, 1340, 890 cm–1.
1H NMR (300 MHz): d = 8.55–8.53 (m, 1 H), 8.45–8.42 (m, 1 H),
8.05 (d, J = 8.7 Hz, 1 H), 7.39–7.31 (m, 2 H), 7.23–7.20 (m, 3 H),
6.11 (br s, 2 H).
13C NMR (125 MHz): d = 153.0, 149.2, 139.9, 137.2, 133.5, 132.2,
132.1, 129.9, 128.9, 126.2, 126.1, 124.0, 113.5, 88.8.
19F NMR (282 MHz): d = –63.5.
References
(1) (a) Buntain, I. G.; Hatton, L. R.; Hawkins, D. W.; Pearson,
C. J.; Roberts, D. A. Eur. Pat. Appl. 295117 A1, 1988;
Chem. Abstr. 1990, 112, 35845. (b) Wu, T.-T. US Patent
5814652, 1998; Chem. Abstr. 1998, 129, 256473.
LRMS (EI, 70 eV): m/z (%) = 374 (10), 373 (M+ + 2, 41), 372 (26),
371 (M+, 100), 336 (3), 325 (11).
(c) Caboni, P.; Sammelson, R. E.; Casida, J. E. J. Agric.
Food Chem. 2003, 24, 7055. (d) Wang, Y.;
HRMS (EI): m/z calcd for C16H1035ClN5O2S (M+): 371.0244; found:
Chackalamannil, S.; Hu, Z.; Clader, J. W.; Greenlee, W.;
Billard, W.; Binch, H. III; Crosby, G.; Ruperto, V.; Duffy,
R. A.; McQuade, R.; Lachowicz, J. Bioorg. Med. Chem. Lett.
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G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med.
Chem. 2006, 49, 947.
371.0243.
20
Yellow solid; mp 150.0–152.3 °C.
IR (KBr): 3444, 3367, 2243, 1614, 1507, 1336, 850 cm–1.
1H NMR (300 MHz): d = 8.46 (d, J = 9.0 Hz, 2 H), 8.05 (d, J = 9.0
Hz, 2 H), 7.39–7.18 (m, 5 H), 6.09 (br s, 2 H).
LRMS (EI, 70 eV): m/z (%) = 339 (M+ + 2, 6), 338 (20), 337 (M+,
(2) (a) Metzner, P.; Thuillier, A. In Sulfur Reagents in Organic
Synthesis; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.,
Eds.; Academic Press: San Diego, 1994. (b) Kondo, T.;
Mitsudo, T. Chem. Rev. 2000, 100, 3205. (c) Ley, S. V.;
Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
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Synlett 2004, 1254. (j) Gendre, F.; Yang, M.; Diaz, P. Org.
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Tetrahedron Lett. 2006, 47, 1217. (l) Zhu, D.; Xu, L.; Wu,
F.; Wan, B. Tetrahedron Lett. 2006, 47, 5781. (m) Chen,
Y.-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609. (n) Wang, Z.;
Mo, H.; Bao, W. Synlett 2007, 91. (o) Lv, X.; Bao, W.
J. Org. Chem. 2007, 72, 3863. (p) Kabir, M. S.; Van Linn,
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(q) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587. (r) Sperotto,
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100).
HRMS (EI): m/z calcd for C16H11N5O2S (M+): 337.0634; found:
337.0633.
21
Yellow solid; mp 166.8–169.0 °C.
IR (KBr): 3444, 3334, 2243, 1618, 1524, 1344, 878 cm–1.
1H NMR (300 MHz): d = 8.43 (d, J = 9.0 Hz, 2 H), 8.01 (d, J = 9.0
Hz, 2 H), 7.51 (d, J = 5.0 Hz, 1 H), 7.35 (s, 1 H), 7.07 (d, J = 6.3
Hz, 1 H), 6.07 (br s, 2 H).
13C NMR (125 MHz): d = 151.4, 146.8, 143.0, 131.7, 130.7, 128.6,
128.2, 125.3, 125.2, 123.5, 113.6, 93.9.
LRMS (EI, 70 eV): m/z (%) = 345 (M+ + 2, 14), 344 (31), 343 (M+,
100).
HRMS (EI): m/z calcd for C14H9N5O2S2 (M+): 343.0198; found:
343.0198.
22
White solid; mp 168.1–170.1 °C.
IR (KBr): 3448, 3338, 2925, 2251, 1626, 1520, 1340, 890 cm–1.
1H NMR (300 MHz): d = 8.54 (s, 1 H), 8.43 (d, J = 8.1 Hz, 1 H),
8.05 (d, J = 8.8 Hz, 1 H), 7.33–7.31 (m, 2 H), 7.23–7.20 (m, 3 H),
6.10 (br s, 2 H).
Synthesis 2009, No. 6, 921–928 © Thieme Stuttgart · New York