The Journal of Organic Chemistry
Note
Hz, 3H), 1.34−1.41 (m, 2H), 1.69−1.76 (m, 2H), 3.90 (t, JH−H = 7.2
Hz, 2H), 7.42−7.47 (m, 1H), 7.63−7.68 (m, 1H), 7.77 (d, JH−H = 8.2
Hz, 1H), 7.93 (d, JH−H = 7.9 Hz, 1H). 13C NMR (methanol-d4, 75
MHz): δ 13.9, 20.7, 32.6, 44.7, 122.1, 125.6, 126.8, 126.9, 133.2, 142.2,
167.1. IR (KBr) νmax: 2958, 1662, 1447, 740, 674 cm−1. ESI-MS: [M +
H]+ m/z 208.3.
bryakov, E. A.; Kislitsin, P. G.; Semenov, V. V.; Zlotin, S. G. Synthesis
2001, 1659.
(5) Recent one-pot reactions based on copper-catalyzed C−N
coupling, for example: (a) Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int.
Ed. 2007, 46, 2598. (b) Zheng, N.; Buchwald, S. L. Org. Lett. 2007, 9,
4749. (c) Martín, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int.
2,6-Dimethylbenzisothiazol-3(2H)-one (3h). White solid, 38
mg (45% yield). Mp: 79−80 °C. 1H NMR (methanol-d4, 300 MHz): δ
2.46 (s, 3H), 3.40 (s, 3H), 7.25 (d, JH−H = 8.2 Hz, 1H), 7.53 (s, 1H),
7.79 (d, JH−H = 7.9 Hz, 1H). 13C NMR (methanol-d4, 75 MHz): δ
21.9, 30.7, 121.7, 122.9, 126.5, 128.4, 142.4, 144.5, 167.4. IR (KBr)
νmax: 2923, 1642, 1331, 754, 669 cm−1. ESI-MS: [M + H]+ m/z 180.1.
HRMS calcd for C9H9NOS: 180.0478 (M + H)+, found 180.0480.
2-Butyl-6-methylbenzisothiazol-3(2H)-one (3i). Colorless oil,
55 mg (50% yield). 1H NMR (methanol-d4, 300 MHz): δ 0.95 (t, JH−H
= 7.2 Hz, 3H), 1.33−1.41 (m, 2H), 1.67−1.75 (m, 2H), 2.46 (s, 3H),
3.87 (t, JH−H = 6.9 Hz, 2H), 7.26 (d, JH−H = 8.2 Hz, 1H), 7.55 (s, 1H),
7.80 (d, JH−H = 8.2 Hz, 1H). 13C NMR (methanol-d4, 75 MHz): δ
13.9, 20.7, 21.9, 32.6, 44.6, 121.8, 123.3, 126.6, 128.4, 142.5, 144.5,
167.1. IR (KBr) νmax: 2959, 1662, 1457, 760, 671 cm−1. ESI-MS: [M +
H]+ m/z 222.1. HRMS calcd for C12H15NOS: 222.0947 (M + H)+,
found 222.0949.
́ ́
Ed. 2006, 45, 7079. (d) Vina, D.; del Olmo, E.; Lopez-Perez, J. L.;
̃
Feliciano, A. S. Org. Lett. 2007, 9, 525. (e) Cacchi, S.; Fabrizi, G.;
Parisi, L. M. Org. Lett. 2003, 5, 3843. (f) Tanimori, S.; Ura, H.;
Kirihata, M. Eur. J. Org. Chem. 2007, 3977. (g) Wang, F.; Zhao, P.; Xi,
C. Tetrahedron Lett. 2011, 52, 231. (h) Saha, P.; Ramana, T.; Purkait,
N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74,
8719. (i) Lv, X.; Bao, W. J. Org. Chem. 2009, 74, 5618. (j) Wang, F.;
Cai, S.; Liao, Q.; Xi, C. J. Org. Chem. 2011, 76, 3174.
(6) For recent one-pot reactions based on copper-catalyzed C−O
coupling, see: (a) Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem.
2007, 72, 5337. (b) Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc.
2003, 125, 4978. (c) Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org.
Chem. 2008, 73, 3452.
(7) Recent results based on copper-catalyzed C−S coupling:
(a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002,
4, 2803. (b) Gonzalez-Arellano, C.; Luque, R.; Macquarrie, D. J. Chem.
Commun. 2009, 1410. (c) Jammi, S.; Sakthivel, S.; Rout, L.;
Mukherjee, T.; Mandal, S.; Mitra, R.; Saha, P.; Punniyamurthy, T. J.
Org. Chem. 2009, 74, 1971. (d) Gan, J.; Ma, D. Org. Lett. 2009, 11,
2788. (e) Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587.
(f) Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009, 5897. (g) Zhao,
Q.; Li, L.; Fang, Y.; Sun, D.; Li, C. J. Org. Chem. 2009, 74, 459.
(h) Murru, S.; Ghosh, H.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11,
4254. (i) You, W.; Yan, X.; Liao, Q.; Xi, C. Org. Lett. 2010, 12, 3930.
(j) Guo, Y.-J.; Tang, R.-Y.; Zhao, P.; Li, J.-H. Tetrahedron Lett. 2010,
51, 649. (k) Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew.
Chem., Int. Ed. 2011, 50, 1118.
2,2′-Thiobis(N-phenylbenzamide) (4). Light yellow solid, 37 mg
1
(35% yield). Mp: 219−220 °C. H NMR (DMSO-d6, 300 MHz): δ
7.06−7.11 (m, 2H), 7.25−7.32 (m, 6H), 7.35−7.42 (m, 4H), 7.59−
7.62 (m, 4H), 7.70 (d, JH−H = 7.9 Hz, 2H), 10.45 (s, 2H). 13C NMR
(DMSO-d6, 75 MHz): δ 119.7, 123.7, 127.3, 127.9, 128.7, 130.6,
132.6, 134.2, 139.0, 139.3, 166.3. IR (KBr) νmax: 3054, 1649, 1437,
751, 688 cm−1. ESI-MS: [M + Na]+ m/z 447.3. HRMS calcd for
C26H20N2O2S: 447.1138 (M + Na)+, found 447.1140.
ASSOCIATED CONTENT
■
S
* Supporting Information
(8) (a) Suzuki, H.; Abe, H. Synth. Commun. 1996, 26, 3413.
(b) Bhakuni, B. S.; Balkrishna, S. J.; Kumar, A.; Kumar, S. Tetrahedron
Lett. 2012, 53, 1354.
1H NMR and 13C NMR spectra for compounds 3a−i and 4 and
X-ray data for 3a (CIF). This material is available free of charge
(9) For recent reviews, see: (a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
(b) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.
(c) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.
(10) X-ray data for 3a: empirical formula: C7H5NOS; unit cell
parameters: a = 6.9074(14) Å, b = 8.0365(16) Å, c = 12.211(2) Å, α =
101.66(3)°, β = 92.96(3)°, γ = 96.79(3)°; space group P-1.
(11) Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011,
13, 454.
AUTHOR INFORMATION
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Corresponding Author
Notes
(12) (a) Clark, J. H.; Jones, C. W.; Duke, C. V. A.; Miller, J. M. J.
Chem. Soc., Chem. Commun. 1989, 81. (b) Sayyahi, S. Synlett 2009,
2035. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P.
V. Mendeleev Commun. 2006, 16, 250.
(13) (a) Morikami, A.; Takimiya, K.; Aso, Y.; Otsubo, T. Org. Lett.
1999, 1, 23. (b) Shimizu, T.; Sakamaki, K.; Miyasaka, D.; Kamigata, N.
J. Org. Chem. 2000, 65, 1721.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the National Natural Science
Foundation of China (20972085 and 21032004) and the
National Basic Research Program of China (2012CB933402).
(14) Uchida, Y.; Kozuka, S. Bull. Chem. Soc. Jpn. 1982, 55, 1183.
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