202
MOLCHANOV et al.
spectrum, d, ppm: 1.491.56 m (1H), 1.862.02 m (3H),
3.43 d (1H, J 8.0 Hz), 3.63 s (3H), 3.66 d (1H, J 8.0 Hz),
4.82 s (1H), 7.29 d (2H, J 8.0 Hz), 7.46 d (2H, J 8.0 Hz).
13C NMR spectrum, d, ppm: 11.95 (CH2), 19.95 (CH),
23.78 (CH), 50.79 (CH), 52.67 (CH3), 53.90 (CH),
83.84 (CH), 106.81 (C), 128.02 (CH), 129.76 (CH),
130.48 (C), 135.03 (C), 171.57 (CO), 174.17 (CO),
201.10 (CO). Found, %: C 58.66; H 4.14; N 3.94.
C17H14ClNO5. Calculated, %: C 58.72; H 4.06; N 4.03.
The study was carried out under financial support of
the Ministry of Education of the Russian Federation
(grant no. A03.-2.11-116) and INTAS program (grant
no. 00-0549).
REFERENCES
1. Padwa,A. and Weingarten, M.D., Chem. Rev., 1996, p. 223;
Mehta, G. and Muthusamy, S., Tetrahedron, 2002, vol. 58,
p. 9477.
X-ray diffraction study of compound Va.
2. Padwa,A., Curtis, E.A., and Sandanayaka, V.P., J. Org. Chem.,
1997, vol. 62, p. 1317; Curtis, E.A., Sandanayaka, V.P., and
Padwa, A., Tetrahedron Lett., 1995, vol. 36, p. 1989;
McMorris, T.C., Hu, Y., Yu, J., and Kelner, M.J., Chem.
Commun., 1997, 315; Kinder, F.R. and Bair, K.W., J. Org.
Chem., 1994, vol. 59, p. 6965; McMills, M.C., Zhuang, L.,
Wright, D.L., and Watt, W., Tetrahedron Lett., 1994, vol. 35,
p. 8311; Dauben, W.G., Dinges, J., and Smith, T.C., J. Org.
Chem., 1993, vol. 58, p. 7635; Padwa, A., Precedo, L., and
Semones, M.A., J. Org. Chem., 1999, vol. 64, p. 4079; Pad-
wa, A, Harring, S.R., and Semones, M, A., J. Org. Chem.,
1998, vol. 63, p. 44; Padwa,A., Broadney, M.A., Marino, J.P.,
and Sheehan, S.M., J. Org. Chem., 1997, vol. 62, 78; Pad-
wa, A., and Price,A.T., J. Org. Chem., 1998, vol. 63, p. 556;
Kissel, W.S. and Padwa,A., Tetrahedron Lett., 1999, vol. 40,
p. 4003.
3. Hodgson, D.M., Stupple, P.A., and Johnstone, C.,
Tetrahedron Lett., 1997, vol. 38, p. 6471; Doyle, M.P. and
Forbes, D.C., Chem. Rev., 1998, vol. 98, p. 911; Suga, H.,
Ishida, H., and Ibata, T., Tetrahedron Lett., 1998, vol. 39,
3165; Kitagaki, S., Anada, M., Kataoka, O., Matsuno, K.,
Umeda, C., Watanabe, N., and Hashimoto, S., J. Am. Chem.
Soc., 1999, vol. 121, p. 1417; Hodgson, D.M., Stupple, P.A.,
and Johnstone, C., Chem. Commun., 1999, p. 2185; Hodgson,
D.M., Stupple, P.A., Pierard, F.Y.T.M., Labande, A.H., and
Johnstone, C., Chem. Eur. J., 2001, vol. 7, p. 4465; Hodg-
son, D.M., Glen, R., Grant, G.H., and Redgrave,A.J., J. Org.
Chem., 2003, vol. 68, p. 581.
4. Padwa,A., Curtis, E.A., and Sandanayaka, V.P., J. Org. Chem.,
1996, vol. 61, p. 73.
5. Molchanov,A.P., Diev, V.V., Kopf, Yu., and Kostikov, R.R.,
Zh. Org. Khim., 2004, vol. 40, p. 258.
6. Ueda, K., Ibata, T. and Takebayashi, M., Bull. Chem. Soc.
Jpn., 1972, vol. 45, p. 2779; Ibata, T. and Jitsuhiro, K., Bull.
Chem. Soc. Jpn., 1979, vol. 52, p. 3582; Ibata, T., Jitsuhi-
ro, K., and Tsubokura, Y., Bull. Chem. Soc. Jpn., 1981,
vol. 54, p. 240; Ibata, T. and Toyoda, J., Bull. Chem. Soc.
Jpn., 1985, vol. 58, p. 1787; Ibata, T., Nakano, H., and Tamu-
ra, H., Bull. Chem. Soc. Jpn., 1992, vol. 65, p. 1362.
7. Kitagaki, S., Yasugahira, M.,Anada, M., Nakajima, M., and
Hashimoto, S., Tetrahedron Lett., 2000, vol. 41, p. 5931.
C29H23NO5. M 465.48. Monoclinic space group P1 21/c1
°
(no 14); a 8.8729(7), b 28.764(2), c 8.6987(7) A,
°
1
b96.06°, V2207.7(3) A3, Z4, dc 1.400 g/cm3, m0.078 mm ,
°
F(000) 912, radiation source MoKa, l 0.71073 A, graphite
monochromator. Further are given some bond lengths (A)
°
and bond angles (deg): C1C2 1.530(2), C2C3 1.512(2),
C3N4 1.390(2), N4C5 1.386(2), C5C6 1.507(2), C6
C2 1.526(2), C6C7 1.574(2), C7C8 1.511(2), C8C9
1.501(2), C9C10 1.520(2), C8C10 1.517(2), C10C11
1.482(2), C1C11 1.516(2), C7O12 1.420(2), C1O12
1.423(2); C2C3N4 108.48(11), C3N4C5 112.37(11),
N4C5C6 108.51(11), C5C6C2 104.77(10), C6C2C3
104.65(11), C1C2C6 103.86(10), C2C6C7 103.26(10),
C6C7O12 103.37(10), C7O12C1 105.49(9), O12C1C2
102.61(10), O12C7C8 109.78(10), C7C8C10 114.1(1),
C8C10C11 118.06(11), C10C11C1 116.06(11), C11C1O12
110.73(10), C8C9C10 60.27(9), C9C8C10 60.49(9),
C8C10C9 59.24(9). Complete set of crystallographic
parameters is deposited in the Database of the Cambridge
Crystallographic Centre (CCDC-254381).
X-ray diffraction study of compound VI. C19H16O3.
M 292.32. Triclinic space group P-1 (no 2); a 10.8897(13),
°
b 11.5437(14), c11.7311(14) A, a 91.98, b98.82, g90.34°,
°
1
V 1456.26(30) A3, Z 4, dc 1.333 g/cm3, m 0.078 mm ,
F(000) 912, radiation source MoKa, l 0.71073A, graphite
monochromator. Further are given some bond lengths
°
(A) and bond angles (deg): C1C1a 1.524(2), C1C7a
1.512(3), C1aC1b 1.504(2), C1bC2 1.334(2), C2C3
1.443(2), C3C4 1.342(2), C4C5 1.441(3), C5C6
1.330(3), C6C6a 1.498(2), C6aC7 1.522(3), C7C7a
1.490(3); C1C7aC1a 60.14(9), C1C1aC7a 59.36(9),
C1aC1C7a 60.50(9), C1aC7aC7 107.44(11), C1aC1bC6a
111.02(11), C1bC1aC7a 106.31(11), C1bC2C3 125.51(12),
C1bC6aC7 104.51(10), C1bC6aC6 111.17(11), C2C1bC6a
124.66(12), C2C3C4 126.91(13), C3C4C5 126.18(14),
C4C5C6 126.63(14), C5C6C6a 123.28(14), C6aC7C7a
110.61(12). Complete set of crystallographic parameters
is deposited in the Database of the Cambridge
Crystallographic Centre (CCDC-254380).
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 2 2005