M. Yoshida et al. / Tetrahedron 67 (2011) 9993e9997
9997
1603, 1267 cmꢁ1. HRMS [EI] calcd for C16H12O3 252.0786, found
References and notes
252.0774.
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4.3.2. 5-Methoxy-2-(3,4-dimethoxy)phenyl-4H-chromen-4-one
(1p). Yield: 45%, white solid: mp 212e214 ꢀC (lit.21 204e206 ꢀC). 1H
NMR (400 MHz, CDCl3)
d
7.58 (t, 1H, J¼3.2 Hz), 7.54 (dd, 1H, J¼8.8,
2.4 Hz), 7.55 (d, 1H, J¼2.4 Hz), 7.14 (dd, 1H, J¼8.4, 1.2 Hz), 6.98 (d,
1H, J¼8.8 Hz), 6.83 (d, 1H, J¼8.4 Hz), 6.69 (s, 1H), 4.01 (s, 3H), 3.98
(s, 3H), 3.97 (s, 3H). 13C NMR (100 MHz, CDCl3)
d 178.3, 161.0, 159.7,
151.8, 151.7, 149.2, 133.5, 123.8, 119.6, 114.4, 111.0, 108.6, 107.9, 106.3,
56.4, 56.0. FTIR (neat) 3423, 2922, 1632, 1601, 1263, 1100 cmꢁ1
.
HRMS [EI] calcd for C18H16O5 312.0998, found 312.0989.
4.3.3. 2,5-Diphenyl-4H-chromen-4-one (1q). Yield: 50%, white solid:
mp 152e153 ꢀC (lit.22 152e154 ꢀC). 1H NMR (400 MHz, CDCl3)
d 7.93
(m, 2H), 7.66 (t, 1H, J¼8.0 Hz), 7.58 (d, 1H, J¼8.0 Hz), 7.52 (m, 3H),
7.39 (m, 3H), 7.34 (m, 2H), 7.21 (d,1H, J¼8.0 Hz), 6.68 (s,1H).13C NMR
(100 MHz, CDCl3) d 178.2, 161.8, 157.4, 143.2, 141.2, 132.4, 131.6, 131.4,
129.0, 128.6, 126.3, 127.4, 127.0, 126.2, 121.3, 117.7, 108.8. FTIR (neat)
3582, 3402, 3068, 1648, 1597, 1367 cmꢁ1. HRMS [FAB] calcd for
C21H15O2 (MþH)þ 299.1072, found 299.1090.
4.3.4. 5-Methyl-2-phenyl-4H-chromen-4-one (1r). Yield: 13%, white
solid: mp 133e135 ꢀC (lit.23 129e130 ꢀC). 1H NMR (400 MHz, CDCl3)
d
7.90 (m, 2H), 7.51 (m, 4H), 7.39 (d, 1H, J¼8.4 Hz), 7.13 (d, 1H,
J¼8.0 Hz), 6.73 (s, 1H), 2.89 (s, 3H). 13C NMR (100 MHz, CDCl3)
d
180.6, 161.5, 157.7, 141.0, 132.6, 131.6, 131.3, 128.9, 127.7, 126.1, 122.3,
116.0, 108.8, 22.7. FTIR (neat) 3586, 3392, 2923, 1653, 1295 cmꢁ1
.
HRMS [FAB] calcd for C16H13O2 (MþþH) 237.0916, found 237.0914.
10. Yoshida, M.; Fujino, Y.; Doi, T. Org. Lett. 2011, 13, 4526e4529.
11. Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
12. Baylis, A. B.; Hillman, M. E. D. Chem. Abstr. 1972, 77, 34174q.
4.3.5. 2-Phenyl-5-trifluoromethanesulfonyloxy-4H-chromen-4-one
(1s). Yield: 83%, white solid: mp 121e122 ꢀC (lit.22 122e123 ꢀC). 1H
NMR (400 MHz, CDCl3)
(dd, 1H, J¼8.4, 0.8 Hz), 7.54 (m, 3H), 7.23 (d, 1H, J¼8.4 Hz), 6.80 (s,
1H). 13C NMR (100 MHz, CDCl3)
176.0, 162.8, 157.2, 146.8, 133.3,
d
7.89 (m, 2H), 7.72 (t, 1H, J¼8.4 Hz), 7.65
13. (a) Ciganek, E. The catalyzed
activated olefins (the MoritaeBayliseHillman reaction) In. Organic Reactions;
Paquette, L. A., Ed.; John Wiley Sons: New York, NY, 1997; Vol. 51,
a-hydroxyalkylation and a-aminoalkylation of
&
d
pp 201e350; (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103,
811e892; (c) Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36,
1581e1588.
132.1, 130.8, 129.2, 126.3, 119.1, 118.9 (q, J¼322 Hz), 118.8, 117.8,
108.7. FTIR (neat) 3582, 3362, 2922, 1646, 1624, 1207 cmꢁ1. HRMS
[EI] calcd for C16H9F3O5S 370.0123, found 370.0120.
14. (a) Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Kishi, Y. Tetrahedron
Lett. 1986, 27, 4763e4766; (b) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron
Lett. 1986, 27, 4767e4770; (c) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwa-
mura, T.; Watanabe, S. Angew. Chem., Int. Ed. 2000, 39, 2358e2360; (d) Wei,
H.-X.; Kim, S. H.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56,
2397e2401; (e) Wei, H.-X.; Gao, J. J.; Li, G. Tetrahedron Lett. 2001, 42,
9119e9122; (f) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T. Tetra-
hedron Lett. 2002, 43, 7039e7041.
15. Hori, K.; Sadatomi, H.; Miyamoto, A.; Kuroda, T.; Sumimoto, M.; Yamamoto, H.
Molecules 2010, 15, 8289e8304.
16. In classification of reaction integration, tandem reaction is categorized as a time
and space integration by the Yoshida group, see; Suga, S.; Yamada, D.; Yoshida,
J. Chem. Lett. 2010, 39, 404e406.
4.3.6. 2-Phenyl-4H-naphtho[1,2-b]pyran-4-one (7d). Yield: 93%,
white solid: mp 158e160 ꢀC (lit.24 159e161 ꢀC). 1H NMR (400 MHz,
CDCl3)
1H), 7.79 (d, 1H, J¼8.6 Hz), 7.72 (m, 2H), 7.59 (m, 3H), 6.98 (s, 1H).
13C NMR (100 MHz, CDCl3)
178.3, 162.7, 153.6, 136.0, 132.0, 131.0,
d
8.64 (m, 1H), 8.18 (d, 1H, J¼8.6 Hz), 8.04 (m, 2H), 7.95 (m,
d
129.2, 129.1, 128.5, 127.2, 126.5, 125.4, 124.5, 122.3, 120.8, 120.3,
108.8. FTIR (neat) 3446, 1642, 1388, 1020 cmꢁ1. HRMS [ESI] calcd for
C19H12O2Na 295.0730 (MþNa)þ, found 295.0712.
17. Streuli, C. A. Anal. Chem. 1960, 32, 985e987.
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Acknowledgements
This work was partially supported by a Grant-in-Aid for Scien-
tific Research on Innovative Areas (No. 2105, 22106503) and Global
COE program (International Center of Research & Education for
Molecular Complex Chemistry) from MEXT. We also thank the
Circle for the Promotion of Science and Engineering for financial
support. It is also grateful for financial support to emergency res-
toration from Astellas Foundation for Research on Metabolics Dis-
orders toward early recovery from the Great East Japan Earthquake.