2434
C.-H. Lin et al. / Tetrahedron Letters 54 (2013) 2431–2434
H
H
N
O
N
O
O
O
hv
O
CHCl3
O
N
O
H
N
2 h, 80%
1b
9
H
N
hv
No reaction
CHCl3
N
O
O
10
Scheme 4. Photochemical reactions of 1b and 10.
hv
O*
O
R
Ph
R
Ph
1b
1c
H
Ph
N
O
O
isc
Ph
3O2
1b
δ+
+
1O2
Ph
3O2
+
1b
H3C
δ−
N
O
1O2
CH3
H
N
exciplex
R=
H3C
N
CH3
O
O
H
H
Ph
Ph
N
H
N
O
O
O
Ph
Ph
O
C
H
H2C
H
+
N
CH3
O
O
O
N
CH3
O
O
HO
1d
1e
-H2O
9
Scheme 5. Proposed photooxidation mechanism.
2. Traven, V. F.; Manaev, A. V.; Safronova, O. B.; Chibisova, T. A.; Lysenko, K. A.;
Antipin, M. Y. Russ. J. Gen. Chem. 2000, 70, 798–808.
Acknowledgments
3. Traven, V. F.; Safronova, O. B.; Vorob’eva, L. I.; Chibisova, T. A.; Senchenya, I. N.
Russ. J. Gen. Chem. 2000, 70, 793–797.
We thank the National Science Council of the Republic of China,
Taiwan, for financially supporting this research under Contract No.
NSC 100-2113-M-029-005-MY2. We also thank the reviewers for
their suggestions and comments.
4. (a) Lin, C. T.; Shih, J. H.; Chen, C. L.; Yang, D. Y. Tetrahedron Lett. 2005, 46, 5033–
5037; (b) Lin, S. L.; Kuo, P. Y.; Yang, D. Y. Molecules 2007, 12, 1316–1324.
5. Kuo, P. Y.; Chuang, R. R.; Yang, D. Y. Mol. Divers. 2009, 13, 253–260.
6. (a) Chen, Y. S.; Kuo, P. Y.; Shie, T. L.; Yang, D. Y. Tetrahedron 2006, 62, 9410–
9416; (b) Lin, J. H.; Lin, C. H.; Yang, D. Y. Tetrahedron Lett. 2012, 53, 778–782.
7. Liao, Y. X.; Kuo, P. Y.; Yang, D. Y. Tetrahedron Lett. 2003, 44, 1599–1602.
8. Crystallographic data (excluding structure factors) for 1b, 4, 5a, 5b, and 6 have
been deposited with the Cambridge Crystallographic Data Centre as
Supplementary data
supplementary publication number CCDC-669310, -880563, -880564,
921695, and -880565, respectively. These data can be obtained free of charge
-
Supplementary data (synthesis of compounds 1a,b, 3a,b, and
4–10 experimental details, additional spectra, and X-ray crystal
structure for 5a) associated with this article can be found, in the
request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic
Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
9. Akhrem, A. A.; Lakhvich, F. A.; Budai, S. I.; Khlebnicova, T. S.; Petrusevich, I. I.
Synthesis 1978, 12, 925–927.
10. Sajimon, M. C.; Ramaiah, D.; Suresh, C. H.; Adam, W.; Lewis, F. D.; George, M. V.
J. Am. Chem. Soc. 2007, 129, 9439–9445.
References and notes
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