H
T. Liu et al.
Paper
Synthesis
was added and the mixture was stirred at r.t. for 30 min. Then nitrone
3b (59 mg, 0.3 mmol, 1.2 equiv) was added followed by tolane (5; 45
mg, 0.25 mmol, 1.0 equiv). The resulting mixture was stirred at 100 °C
for 12 h. After cooling to r.t., the solvent was removed under reduced
pressure and the residue was purified by silica gel chromatography
using PE/EtOAc to afford the desired product 6 as a fluorescent yellow
liquid; yield: 53.8 mg (80%).
1H NMR (600 MHz, CDCl3): δ = 8.12 (s, 1 H), 7.60 (d, J = 7.8 Hz, 1 H),
7.37–7.33 (m, 5 H), 7.27 (t, J = 7.8 Hz, 2 H), 7.25–7.19 (m, 4 H), 7.18–
7.15 (m, 1 H), 7.07 (t, J = 7.2 Hz, 1 H).
(5) (a) Floyd, R. A. Proc. Soc. Exp. Biol. Med. 1999, 222, 236.
(b) Zhang, H.; Joseph, J.; Vasquez-Vivar, J.; Karoui, H.;
Nsanzumuhire, C.; Martasek, P.; Tordo, P.; Kalyanaraman, B.
FEBS Lett. 2000, 473, 58. (c) Bottle, S. E.; Hanson, G. R.; Micallef,
A. S. Org. Biomol. Chem. 2003, 1, 2585. (d) Bottle, S. E.; Micallef,
A. S. Org. Biomol. Chem. 2003, 1, 2581. (e) Hatano, B.; Sato, H.;
Ito, T.; Ogata, T. Synlett 2007, 2130. (f) Wang, F.; Burck, M.;
Diesendruck, C. E. ACS Macro Lett. 2017, 6, 42.
(6) Floyd, R. A. Aging Cell 2006, 5, 51.
(7) (a) Gella, C.; Ferrer, E.; Alibes, R.; Busque, F.; de March, P.;
Figueredo, M.; Font, J. J. Org. Chem. 2009, 74, 6365. (b) Goti, A.;
De Sarlo, F.; Romani, M. Tetrahedron Lett. 1994, 35, 6571.
(c) Goti, A.; Nannelli, L. Tetrahedron Lett. 1996, 37, 6025.
(d) Hou, H.; Zhu, S.; Pan, F.; Rueping, M. Org. Lett. 2014, 16,
2872. (e) Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. J. Org.
Chem. 1996, 61, 8099. (f) Soldaini, G.; Cardona, F.; Goti, A. Org.
Lett. 2007, 9, 473. (g) Colladon, M.; Scarso, A.; Strukul, G. Green
Chem. 2008, 10, 793. (h) Singh, B.; Jain, S. L.; Khatri, P. K.; Sain, B.
Green Chem. 2009, 11, 1941. (i) Yudha, S. S.; Kusuma, I.; Asao, N.
Tetrahedron 2015, 71, 6459. (j) Mirza-Aghayan, M.; Tavana, M.
M.; Boukherroub, R. Tetrahedron Lett. 2014, 55, 5471.
(k) Nikbakht, F.; Heydari, A.; Saberi, D.; Azizi, K. Tetrahedron
Lett. 2013, 54, 6520. (l) Abrantes, M.; Gonçalves, I. S.; Pillinger,
M.; Vurchio, C.; Cordero, F. M.; Brandi, A. Tetrahedron Lett. 2011,
52, 7079. (m) Singh, B.; Jain, S. L.; Rana, B. S.; Khatri, P. K.; Sinha,
A. K.; Sain, B. ChemCat Chem 2010, 2, 1260. (n) Zonta, C.;
Cazzola, E.; Mba, M.; Licini, G. Adv. Synth. Catal. 2008, 350, 2503.
(8) (a) Saladino, R.; Neri, V.; Cardona, F.; Goti, A. Adv. Synth. Catal.
2004, 346, 639. (b) Cicchi, S.; Corsi, M.; Goti, A. J. Org. Chem.
1999, 64, 7243. (c) Cicchi, S.; Marradi, M.; Goti, A.; Brandi, A.
Tetrahedron Lett. 2001, 42, 6503. (d) Matassini, C.; Parmeggiani,
C.; Cardona, F.; Goti, A. Org. Lett. 2015, 17, 4082. (e) D’Adamio,
G.; Parmeggiani, C.; Goti, A.; Cardona, F. Eur. J. Org. Chem. 2015,
6541. (f) Prakash, P.; Gravel, E.; Nguyen, D.-V.; Namboothiri, I.
N. N.; Doris, E. ChemCatChem 2017, 9, 2091. (g) Parmeggiania,
C.; Matassini, C.; Cardona, F.; Goti, A. Synthesis 2017, 49, 2890.
(9) (a) Morales, S.; Guijarro, F. G.; Alonso, I.; Ruano, J. L. G.; Cid, M.
B. ACS Catal. 2016, 6, 84. (b) Torrente, S.; Noya, B.; Branchadell,
V.; Alonso, R. J. Org. Chem. 2003, 68, 4772. (c) Pfeiffer, J. Y.;
Beauchemin, A. M. J. Org. Chem. 2009, 74, 8381. (d) Grigor’ev, I.
A. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis;
Feuer, H., Ed.; Wiley: Hoboken, 2008, 129–434.
(10) (a) LeBel, N. A.; Balasubramanian, N. Tetrahedron Lett. 1985, 26,
4331. (b) Nakama, K.; Seki, S.; Kanemasa, S. Tetrahedron Lett.
2001, 42, 6719. (c) Grigg, R.; Markandu, J.; Surendrakumar, S.
Tetrahedron Lett. 1990, 31, 1191. (d) Ma, X.-P.; Shi, W.-M.; Mo,
X.-L.; Li, X.-H.; Li, L.-G.; Pan, C.-X.; Chen, B.; Su, G.-F.; Mo, D.-L. J.
Org. Chem. 2015, 80, 10098. (e) Wu, S.-Y.; Ma, X.-P.; Liang, C.;
Mo, D.-L. J. Org. Chem. 2017, 82, 3232.
(11) (a) Kazemi, F.; Ramdar, M.; Tavana, B.; Davarpanah, F. Monatsh.
Chem. 2017, 148, 1101. (b) Vallee, Y.; Masson, G.; Py, S.;
Cividino, P.; Pandya, U. S.; Chapoulaud, V. G. Synlett 2001, 1281.
(c) Cisneros, L.; Serna, P.; Corma, A. Angew. Chem. Int. Ed. 2014,
53, 9306. (d) Ung, S.; Falguieres, A.; Guy, A.; Ferroud, C. Tetrahe-
dron Lett. 2005, 46, 5913.
(12) (a) Kawade, R. K.; Liu, R.-S. Angew. Chem. Int. Ed. 2017, 56, 2035.
(b) Pagar, V. V.; Liu, R.-S. Angew. Chem. Int. Ed. 2015, 54, 4923.
(c) Reddy, A. R.; Zhou, C.-Y.; Che, C.-M. Org. Lett. 2014, 16, 1048.
(d) Reddy, A. R.; Guo, Z.; Siu, F.-M.; Lok, C.-N.; Liu, F.; Yeung, K.-
C.; Zhou, C.-Y.; Che, C.-M. Org. Biomol. Chem. 2012, 10, 9165.
(e) Pagar, V. V.; Jadhav, A. M.; Liu, R.-S. J. Am. Chem. Soc. 2011,
133, 20728. (f) Wu, M.-Y.; He, W.-W.; Liu, X.-Y.; Tan, B. Angew.
Chem. Int. Ed. 2015, 54, 9409. (g) Molander, G. A.; Cavalcan, L. N.
13C NMR (150 MHz, CDCl3): δ = 135.9, 135.0, 134.1, 132.7, 130.1,
128.75, 128.67, 128.51, 128.2, 127.7, 126.2, 122.7, 120.4, 119.7, 115.1,
110.9.
HRMS (ESI+): m/z [M + H]+ calcd for C20H16N: 270.3490; found:
270.3495.
Supporting Information
Supporting information for this article is available online at
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References
(1) (a) Hamer, J.; Macaluso, A. Chem. Rev. 1964, 64, 473.
(b) Katahara, S.; Kobayashi, S.; Fujita, K.; Matsumoto, T.; Sato, T.;
Chida, N. J. Am. Chem. Soc. 2016, 138, 5246. (c) Gothelf, K. V.;
Jørgensen, K. A. Chem. Rev. 1998, 98, 863. (d) Yang, J. Synlett
2012, 23, 2293.
(2) For selected examples of [3+2] cycloaddition involving nitrone,
see: (a) Shi, Y.; Lin, A.; Mao, H.; Mao, Z.; Li, W.; Hu, H.; Zhu, C.;
Cheng, Y. Chem. Eur. J. 2013, 19, 1914. (b) Jiao, P.; Nakashima, D.;
Yamamoto, H. Angew. Chem. Int. Ed. 2008, 47, 2411.
(c) Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128,
9626. (d) Palomo, C.; Oiarbide, M.; Arceo, E.; Garcia, J. M.; Lopez,
R.; Gonzalez, A. Angew. Chem. Int. Ed. 2005, 44, 6187. (e) Sibi, M.
P.; Ma, Z.-H.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718.
(3) (a) Anderson, L. L. Asian J. Org. Chem. 2016, 5, 9. (b) Zhang, Z.-
M.; Chen, P.; Li, W.; Niu, Y.; Zhao, X.-L.; Zhang, J. Angew. Chem.
Int. Ed. 2014, 53, 4350. (c) Nakamura, I.; Jo, T.; Zhang, D.; Terada,
M. Org. Chem. Front. 2014, 1, 914. (d) Mo, D.-L.; Anderson, L. L.
Angew. Chem. Int. Ed. 2013, 52, 6722. (e) Yeom, H.-S.; Shin, S.
Acc. Chem. Res. 2014, 47, 966. (f) Yeom, H.-S.; Lee, Y.; Lee, J.-E.;
Shin, S. Org. Biomol. Chem. 2009, 7, 4744. (g) Yeom, H.-S.; Lee, Y.;
Jeong, J.; So, E.; Hwang, S.; Lee, J.-E.; Lee, S. S.; Shin, S. Angew.
Chem. Int. Ed. 2010, 49, 1611. (h) Pati, K.; Liu, R.-S. Chem.
Commun. 2009, 5233. (i) Nakamura, I.; Okamoto, M.; Sato, Y.;
Terada, M. Angew. Chem. Int. Ed. 2012, 51, 10816. (j) Gawade, S.
A.; Bhunia, S.; Liu, R.-S. Angew. Chem. Int. Ed. 2012, 51, 7835.
(k) Mo, D.-L.; Wink, D. J.; Anderson, L. L. Chem. Eur. J. 2014, 20,
13217.
(4) (a) Yao, T.; Ren, B.; Wang, B.; Zhao, Y. Org. Lett. 2017, 19, 3135.
(b) Li, Y.; Shan, C.; Yang, Y.-F.; Shi, F.; Qi, X.; Houk, K. N.; Lan, Y. J.
Phys. Chem. A 2017, 121, 4496. (c) Chen, F.; Zhu, F.-F.; Zhang, M.;
Liu, R.-H.; Yu, W.; Han, B. Org. Lett. 2017, 19, 3255. (d) Chen, C.-
H.; Liu, Q.-Q.; Ma, X.-P.; Feng, Y.; Liang, C.; Pan, C.-X.; Su, G.-F.;
Mo, D.-L. J. Org. Chem. 2017, 82, 6417. (e) Saruengkhanphasit,
R.; Collier, D.; Coldham, I. J. Org. Chem. 2017, 82, 6489. (f) Wang,
C.; Wang, D.; Yan, H.; Wang, H.; Pan, B.; Xin, X.; Li, X.; Wu, F.;
Wan, B. Angew. Chem. Int. Ed. 2014, 53, 11940.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–I