Chemistry of Heterocyclic Compounds 2015, 51(10), 903–912
In order to separate the diastereomers 22 and 23, the
mixture was treated at room temperature with CHCl
5 ml), the insoluble precipitate of compound 22 was
filtered off and washed two times with the same amount of
solvent. The filtrate was evaporated under air stream,
providing the pure cycloadduct 23.
References
3
(
1. Tattje, D. H. E.; Bos, R.; Bruins, A. P. Planta Med. 1980, 38, 79.
2
3
4
5
6
. Arnone, A.; Cardillo, R.; Di Modugno, V.; Nasini, G. J.
Chem. Soc., Perkin Trans. 1 1989, 1995.
. Nagase, R.; Katayama, M.; Mura, H.; Matsuo, N.; Tanabe, Y.
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(
6bR*,7R*,10aR*)-8-Acetyl-9-hydroxy-6b-nitro-7-phe-
. Bonnett, R.; Davies, J. E.; Hursthouse, M. B. Nature 1976,
nyl-6b,7,10,10а-tetrahydronaphtho[1,2-c:3,4-c']bis-[1,2,5]-
oxa-diazole 1,4-dioxide (22). Yield 0.12 g (28%), beige
2
62, 326.
. Bojase, G.; Nguyen, T. V.; Payne, A. D.; Willis, A. C.;
Sherburn, M. S. Chem. Sci. 2011, 2, 229.
1
crystals, mp 220–222°С. H NMR spectrum, δ, ppm (J, Hz):
2
3
.09 (3Н, s, COCH ); 2.84 (1Н, dd, J = 10.0, J = 19.8) and
3
. Iyoda, M.; Nakamura, N.; Todaka, M.; Ohtsu, S.; Hara, K.;
Kuwatani, y.; Yoshida, M.; Matsuyama, H., Sugita, M;
Tachibana, H.; Inoue, H. Tetrahedron Lett. 2000, 41, 7059.
.62 (1Н, dd, J = 8.8, J = 19.8, 10-CH ); 4.66 (1Н, dd, J = 8.8,
2
J = 10.0, 10a-CH); 5.46 (1Н, s, 7-CH); 7.30–7.48 (5Н, m, H
13
Ph); 15.90 (1Н, s, OH). C NMR spectrum, δ, ppm: 25.9
COСН ); 30.6 (C-10a); 32.1 (C-10); 44.8 (C-7); 91.0 (C-6b);
03.9 (C-3b); 107.1 (C-8); 111.0 (C-10b); 130.1 (C-4 Ph);
30.2 (C-2,6 Ph); 130.5 (C-3,5 Ph); 136.1 (C-1 Ph); 141.4 (C-
a); 150.1 (C-6a); 176.3 (C-9); 201.6 (COCH ). Found, m/z:
. Calculated, m/z: 450.0656.
6bR*,7S*,10aR*)-8-Acetyl-9-hydroxy-6b-nitro-7-phenyl-
7. Hopf, H.; Sherburn, M. S. Angew. Chem., Int. Ed. 2012, 51,
2298.
(
3
8
9
1
1
. Tsuge, O.; Wada, E.; Kanemasa, S.; Sakon, H. Bull. Chem.
Soc. Jpn. 1984, 57, 3221.
1
1
3
. Kurbatov, S.; Goumont, R.; Marrot, J.; Terrier, F.
Tetrahedron Lett. 2004, 45, 1037.
3
+
4
50.0654 [M+Na] . C18
H
13
N
5
NaO
8
0. Kurbatov, S.; Goumont, R.; Lakhdar, S.; Marrot, J.; Terrier, F.
Tetrahedron Lett. 2005, 61, 8167.
(
6
b,7,10,10а-tetrahydronaptho[1,2-c:3,4-c']bis[1,2,5]oxa-
1. Kurbatov, S.; Lakhdar, S., Goumont, R.; Terrier, F. Org.
Prep. Proced. Int. 2012, 44, 289.
diazole 1,4-dioxide (23). Yield 0.30 g (70%), beige
1
crystals, mp 190–192°С. H NMR spectrum, δ, ppm (J,
12. Sepulcri, P.; Halle, J.-C.; Goumont, R.; Riou, D.; Terrier, F. J.
Org. Chem. 1999, 64, 9254.
Hz): 2.06 (3Н, s, COCH ); 3.19 (1Н, dd, J = 10.1, J = 20.7)
3
and 4.04 (1Н, d, J = 20.7, 10-CH
2
); 5.26 (1Н, d, J = 10.1,
0a-CH); 5.56 (1Н, s, 7-CH); 7.06–7.16 (2Н, m, Н-2,6 Ph);
.25–7.39 (3Н, m, Н-3,4,5 Ph); 16.06 (1H, s, OH).
C NMR spectrum, δ, ppm: 23.2 (C-10); 25.6 (COСН
2.6 (C-10a); 49.4 (C-7); 89.0 (C-6b); 104.4 (C-3b); 106.3
13. (a) Buncel, E.; Terrier, F. Org. Biomol. Chem. 2010, 8, 2285.
(b) Terrier, F.; Dust, J. M.; Buncel, E. Tetrahedron. 2012, 68,
1
7
1829.
1
3
14. Terrier, F.; Kizilian, E.; Halle, J.-C.; Buncel, E. J. Am. Chem.
Soc. 1992, 114, 1740.
3
);
3
1
5. Goumont, R.; Sebban, M.; Sepulcri, P.; Marrot, J.; Terrier, F.
Tetrahedron 2002, 58, 3249.
(
C-8); 108.8 (C-10b); 129.8 (C-3,5 Ph); 130.2 (C-2,6 Ph);
30.6 (C-4 Ph); 135.2 (C-1 Ph); 141.1 (C-3a); 152.8
1
1
6. Steglenko, D. V.; Kletsky, M. E.; Kurbatov, S. V.; Tatarov, A. V.;
Minkin, V. I.; Goumont, R.; Terrier, F. Chem.–Eur. J. 2011,
(
[
C-6a); 176.2 (C-9); 201.8 (COCH
3
). Found, m/z: 426.0693
–
M–Н] . C18
H
12
N
5
O
8
. Calculated, m/z: 426.0691.
1
7, 7592.
X-ray diffraction study of compounds 10, 23, and 22 was
1
7. Lakhdar, S.; Terrier, F.; Vichard, D.; Berionni, G.; El Guesmi, N.;
performed of an Apex II automated diffractometer (graphite
Boubaker, T.; Goumont, R. Chem.–Eur. J. 2010, 16, 5681.
monochromator, λ(MoKα) 0.71073 Å (for compounds 22 and
18. García, J. I.; Mayoral, J. A.; Salvatella, L. Acc. Chem. Res.
2000, 33, 658.
2
3) and λ(СuKα) 1.54178 Å (for compound 10),
1
9. Parr, R. G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc.
ω-scanning). Empirical adjustment for absorption and
correction of systematic errors were performed with the
SADABS program. The structures were solved by direct
method and refined with full matrix method of least
1
999, 121, 1922.
2
0. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and
Molecules; Oxford University Press: New York, 1989.
2
21. Bradford, T. A.; Payne, A. D.; Willis, A. C.; Paddon-Row, M. N.;
squares by F hkl with anisotropic thermal parameters for all
Sherburn, M. S. J. Org. Chem. 2010, 75, 491.
non-hydrogen atoms. The positions of hydrogen atoms
2
2
2. Lyssenko, K. A.; Antipin, M. Yu.; Antonov, D. Yu.
ChemPhysChem 2003, 4, 817.
(
except those belonging to ОН groups) were calculated
geometrically and refined by the "rider" model. The
structures were solved and refined by using the SHELX
3. Bader, R. Atoms in Molecules. A Quantum Theory [Russian
translation]; Mir: Moscow, 2001.
3
7
software package, version 2009-9.13. The complete
crystallographic datasets were deposited at the Cambridge
Crystallographic Data Center (deposits СCDC 1429656
24. Lyssenko, K. A. Mendeleev Commun. 2012, 22, 1.
25. Munoz, E.; Benito, A. M.; Estepa, L. C.; Fernandez, J.;
Maniette, Y.; Martinez, M. T.; de la Fuente, G. F.; Liu, H.;
Silva, C. M.; Macedo, E. A.; Espinosa, E.; Molins, E.;
Lecomte, C. Chem. Phys. Lett. 1998, 285, 170.
(
compound 10), СCDC 1429657 (compound 23), and
СCDC 1429658 (compound 22)).
2
6. Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E.
Chem. Phys. Lett., 2001, 336, 457.
The Supplementary information file containing quantum-
chemical calculation data, as well as the main crystallo-
graphic parameters of structures 10, 22, and 23 are
available online at http://link.springer.com/journal/10593.
2
7. Minkin, V. I.; Tkachuk, A. V.; Kletskii, M. E.; Steglenko, D. V.;
Voronina, V. A.; Kurbatov S. V. Russ. Chem. Bull. 2013, 62,
4
64. [Izv. Akad. Nauk, Ser. Khim. 2013, 2, 464.]
2
8. Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. J. Am. Chem.
Soc. 1989, 111, 1023.
This study was supported by a Russian Scietific Fund
grant (project 14-13-00103).
29. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem.
Soc. 1994, 116, 909.
9
11