none 10.3987/COM-06-10871 CLOCKSS Archive CLOCKSS Archive 5187 37273993 73640 20090409181122 10.13030 2024-06-24T20:44:10Z 2009-04-09T09:15:01Z 7 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2006 68 11 Minoru Ishikura Miyako Hasunuma Koji Yamada Reiko Yanada 2006 2253 COM-06-10871 10.3987/COM-06-10871 20090409181122 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-06-10871 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-06-10871 10.3987/COM-03-9841 1. M. K. Gurjar, S. Bera, R. R. Joshi, and R. A. Joshi, Heterocycles, 2003, 60, 2293; M. Ishikura, M. Hasunuma, and M. Saijo, Heterocycles, 2004, 63, 5; M. Ishikura, M. Hasunuma, and K. Yanada, Heterocycles, 2005, 65, 2587; R. J. Brea, M. Amorin, L. Castedo, and J. R. Granja, Angew. Chem. Int. Ed., 2005, 44, 5710. 10.1016/S0040-4039(99)01910-3 a) N. Katagiri, Y. Yamatoya, and M. Ishikura, Tetrahedron Lett., 1999, 40, 9069; 10.1039/b210963h b) M. Ishikura, A. Murakami, and N. Katagiri, Org. Biomol. Chem., 2003, 1, 452; 10.3987/COM-03-9904 c) M. Ishikura, K. Matsumoto, M. Hasunuma, and N. Katagiri, Heterocycles, 2003, 60, 2737; 10.3987/COM-04-S(P)19 d) M. Ishikura, K. Matsumoto, and A. Murakami, Heterocycles, 2004, 64, 241. 10.3987/COM-00-8902 3. M. Ishikura, S. Kudo, A. Hino, N. Ohnuki, and N. Katagiri, Heterocycles, 2000, 53, 1499. 10.1002/cber.19650981227 4. R. Huisgen, L. Möbius, G. Müller, H. Stangl, G. Szeimies, and J. M. Vernon, Chem. Ber., 1965, 98, 3992. 10.3998/ark.5550190.0003.615 5. There is one example of cycloaddition reaction of phenyl azide to 1 (R=H) at 90°C in CH2Cl2; J. R. Malpass, D. Belkacemi, G. A. Griffith, and M. D. Robertson, ARKIVOC, 2002, (vi), 164. 10.1016/S0040-4020(01)00906-1 6. P. Lidstrom, J. Tierney, B. Wathey, and J. Westman, Tetrahedron, 2001, 57, 9225; M. Larhed, C. Moberg, and A. Hallberg, Acc. Chem. Res., 2002, 35, 717; C. O. Kappa, Angew. Chem. Int. Ed., 2004, 43, 6250. 10.3987/COM-97-7997 7. F. Louërat, K. Bougrin, A. Loupy, A. M. O. Retana, J. Pagalday, and F. Palacios, Heterocycles, 1998, 48, 161. 8. Microwave irradiation was carried out using Green-Motif I (IMCR-25003) microwave reactor (IDX Corporation). To a glass tube were added 1b (1 mmol) and 2a (2 mmol), and the vessel was placed into the cavity of microwave reactor. Microwave irradiation at 300 W was performed, the temperature being ramped from rt to 140°C. The mixture was let stand for 30 min. After cooling, the mixture was separated by medium pressure chromatography (SiO2) with hexane-AcOEt. 10.1016/B978-0-12-633480-7.50008-0 9. N-Acyl azide as a good nitrene precursor: W. Lwowski, “Azides and Nitrenes-Reactivity and Utility,” ed. by E. F. Scriven, Academic Press, London, 1984, pp. 205-246. 10. 3b: 1H-NMR (CDCl3) δ: 0.21 (s, 3H), 0.32 (s, 3H), 0.89 (s, 9H), 1.52 (d, 1H, J=9.7 Hz), 1.86 (d, 1H, J=9.7 Hz), 2.45 (s, 3H), 2.84 (s, 1H), 3.28 (d, 1H, J=6.3 Hz), 3.43 (d, 1H, J=6.3 Hz), 3.94 (s, 1H), 7.35 (d, 2H, J=8.6 Hz), 7.80 (d, 2H, J=8.6 Hz). 13C-NMR (CDCl3) δ: -5.3, -4.9, 18.9, 21.7, 26.3, 33.0, 40.0, 44.1, 47.2, 58.4, 127.9, 129.9, 134.8, 145.0, 181.9. 3d: 1H-NMR (CDCl3) δ: 0.19 (s, 3H), 0.28 (s, 3H), 0.91 (s, 9H), 1.54 (d, 1H, J=9.7 Hz), 1.86 (d, 1H, J=9.7 Hz), 2.82 (s, 1H), 3.25 (s, 1H), 3.28 (s, 1H), 3.86 (s, 1H), 7.18-7.21 (m, 6H), 7.32-7.35 (m, 4H). 13C-NMR (CDCl3) δ: -5.2, -4.8, 18.9, 26.4, 32.6, 37.6, 42.1, 47.3, 58.7, 120.3, 120.4, 125.5, 129.9, 182.6. 5b: 1H-NMR (CDCl3) δ: 0.33 (s, 3H), 0.36 (s, 3H), 0.95 (s, 9H), 1.39 (d, 1H, J=10.9 Hz), 1.94 (d, 1H, J=10.9 Hz), 3.23 (s, 1H), 4.15 (s, 1H), 4.20 (d, 1H, J=9.2 Hz), 5.20 (d, 1H, J=9.2 Hz), 7.08 (t, 1H, J=7.4 Hz), 7.23-7.28 (m, 2H), 7.36 -7.39 (m, 2H). 13C-NMR (CDCl3) δ: -5.2, -4.8, 19.1, 26.3, 35.7, 51.4, 61.4, 62.3, 82.5, 114.0, 123.0, 129.8, 139.7, 181.0. 5c: 1H-NMR (CDCl3) δ: 1.36 (td, 1H, J=1.7, 11.5 Hz), 1.43 (s, 9H), 1.85 (td, 1H, J=1.7, 10.9 Hz), 3.27 (s, 1H), 3.73 (d, 1H, J=9.2 Hz), 4.17 (s, 1H), 4.81 (d, 1H, J=14.9 Hz), 4.91 (d, 1H, J=14.9 Hz), 5.02 (d, 1H, J=9.2 Hz), 7.30-7.40 (m, 5H). 13C-NMR (CDCl3) δ: 28.1, 31.8, 52.1, 53.5, 61.5, 62.2, 83.1, 83.6, 128.4, 128.5, 129.1, 135.9, 148.7, 172.0. 5d: 1H-NMR (CDCl3) δ: -0.12 (s, 3H), 0.12 (s, 3H), 0.80 (s, 9H), 1.38 (d, 1H, J=10.3 Hz), 1.80 (d, 1H, J=10.3 Hz), 3.09 (s, 1H), 3.35 (s, 1H), 3.46 (d, 1H, J=9.7 Hz), 4.64 (d, 1H, J=14.3 Hz), 4.95 (d, 1H, J=14.3 Hz), 4.98 (d, 1H, J=9.7 Hz), 7.31-7.40 (m, 5H). 13C-NMR (CDCl3) δ: -5.4, -5.5, 18.8, 26.2, 35.9, 51.7, 53.8, 62.3, 64.5, 83.2, 128.5, 128.7, 129.1, 135.9, 181.5. 6b: 1H-NMR (CDCl3) δ: 0.32 (s, 3H), 0.34 (s, 3H), 0.96 (s, 9), 1.39 (d, 1H, J=10.9 Hz), 1.92 (d, 1H, J=10.9 Hz), 3.13 (s, 1H), 4.35 (s, 1H), 4.38 (d, 1H, J=9.2 Hz), 5.06 (d, 1H, J=9.2 Hz), 7.06-77.09 (m, 1H), 7.35-7.39 (m, 4H). 13C-NMR (CDCl3) δ: -5.1, -5.08, 18.9, 26.4, 35.8, 51.1, 57.0, 62.6, 88.5, 114.3, 123.1, 129.7, 139.3, 180.8. 6c: 1H-NMR (CDCl3) δ: 1.36 (d, 1H, J=10.9 Hz), 1.50 (s, 9H), 1.90 (d, 1H, J=10.9 Hz), 2.74 (s, 1H), 3.77 (d, 1H, J=9.2 Hz), 4.72 (d, 1H, J=14.9 Hz), 4.85 (s, 1H), 4.96 (d, 1H, J=14.9 Hz), 5.01 (d, 1H, J=9.2 Hz), 7.25-7.37 (m, 5H). 13C-NMR (CDCl3) δ: 28.1, 32.2, 52.1, 53.0, 58.8, 62.1, 83.9, 86.7, 128.3, 128.5, 129.1, 135.4, 148.6, 172.1. 6d: 1H-NMR (CDCl3) δ: 0.23 (s, 3H), 0.25 (s, 3H), 0.90 (s, 9H), 1.38 (d, 1H, J=10.3 Hz), 1.86 (d, 1H, J=10.3 Hz), 2.60 (s, 1H), 3.74 (d, 1H, J=9.3 Hz), 4.21 (s, 1H), 4.70 (d, 1H, J=14.3 Hz), 4.83 (d, 1H, J=9.3 Hz), 4.95 (d, 1H, J=14.3 Hz), 7.27-7.37 (m, 5H). 13C-NMR (CDCl3) δ: -5.2, -5.3, 18.9, 26.3, 36.3, 51.6, 52.7, 58.5, 62.7, 88.8, 128.3, 129.0, 135.8, 181.3.