O. A. Maloshitskaya et al. / Tetrahedron 61 (2005) 7294–7303
7303
2.83 (1H, d, JgemZ15.6 Hz, H-a from CO–CH2), 3.02 (1H,
Acknowledgements
d, JgemZ15.6 Hz, H-b from CO–CH2), 4.08 (2H, m,
CH2CH3), 6.72 (1H, t, J67ZJ78Z7.2 Hz, H-7), 6.79 (1H,
d, J56Z8.4 Hz, H-5), 7.08 (1H, broad s, NH), 7.28 (1H, dt,
J56ZJ67Z8.4 Hz, J68Z1.8 Hz, H-6), 7.45 (1H, d, J78Z
7.2 Hz, H-8), 7.72 (1H, s, SO2NH). dC(DMSO-d6): 13.90
(CH3CH2), 26.08 (CH3), 43.33 (CH2CO), 59.89 (CH2CH3),
68.95 (N–C–N), 116.10 (C-5), 116.38 (C-7), 120.01 (C-8a),
123.42 (C-8), 132.87 (C-6), 142.15 (C-4a), 168.97 (CO).
We thank Dr. V. Ovcharenko for HRMS spectra and fruitful
discussions.
References and notes
4.2.4.5. 2-Methyl-2-(2H,4H-1,1-dioxo-benzo-1,2,4-
thiadiazin-3-yl)acetic acid, tert-butyl ester (22b). Yield
77%, white powder, mp 151 8C. HRMS: C14H20N2O4S MC%
calcd 312.1144; obsd 312.1155. dH(DMSO-d6): 1.40 (9H,
s, (CH3)3C), 1.62 (3H, s, CH3), 2.72 (1H, d, JgemZ15.0 Hz,
H-a from CO–CH2), 2.93 (1H, d, JgemZ15.0 Hz, H-b from
CO–CH2), 6.72 (1H, t, J67ZJ78Z7.2 Hz, H-7), 6.80 (1H, d,
J56Z8.4 Hz, H-5), 7.04 (1H, broad s, NH), 7.28 (1H, dt,
J56ZJ67Z7.8 Hz, J68Z1.8 Hz, H-6), 7.45 (1H, dd, J78Z
8.4 Hz, J68Z1.2 Hz, H-8), 7.67 (1H, s, SO2NH). dC(DMSO-
d6): 26.02 (CH3), 27.61 ((CH3)3C), 44.37 (CH2CO), 69.01
(N–C–N), 80.22 ((CH3)3C), 116.15 (C-5), 116.38 (C-7),
120.11 (C-8a), 123.45 (C-8), 132.84 (C-6), 142.16 (C-4a),
168.40 (CO).
´ ´
1. Lazar, L.; Fu¨lop, F. Eur. J. Org. Chem. 2003, 3025–3042 and
¨
references therein.
2. Maloshitskaya, O.; Sinkkonen, J.; Ovcharenko, V. V.; Zelenin,
K. N.; Pihlaja, K. Tetrahedron 2004, 60, 6913–6921.
3. Sinkkonen, J.; Zelenin, K. N.; Potapov, A.-K.A.; Lagoda, I. V.;
Alekseyev, V. V.; Pihlaja, K. Tetrahedron 2003, 59,
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4. (a) Zelenin, K. N.; Alekseyev, V. V.; Ukraintsev, I. V.;
Tselinsky, I. V. Org. Prep. Proc. Int. 1998, 30, 53–61. (b)
Zelenin, K. N.; Ukraintsev, I. V. Khim. Geterotsikl. Soed.
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5. Goblyos, A.; Lasar, L.; Fulop, F. Tetrahedron 2002, 58,
¨
¨
¨ ¨
1011–1016.
´ ´
¨ ¨
¨ ¨
6. Lazar, L.; Goblyos, A.; Martinek, T. A.; Fulop, F. J. Org.
4.2.4.6. 20-Carbethoxy-2H,4H-spiro(benzo-1,2,4-thia-
diazine-3,10-cyclohexane(-1,1-dioxide (22c) (equatorial
carbethoxy group). Yield 68%, white powder, mp
161 8C. HRMS: C15H20N2O4S MC% calcd 324.1144; obsd
324.1152. dH(DMSO-d6): 1.18 (3H, t, JCH3–CH2Z7.2 Hz,
CH3CH2), 1.34 (2H, m, H-60ax, H-40ax), 1.56 (1H, m,
H-50ax or H-50eq), 1.66 (2H, m, H-40eq,0H-50eq or H-50ax),
1.76 (1H, m, H-30ax), 1.83 (1H, m, H-3 eq), 2.64 (1H, dm,
Chem. 2002, 67, 4734–4741.
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V. V.; Sinkkonen, J.; Pihlaja, K. Chem. Heterocycl. Comp.
2002, 38, 1148–1149.
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Chem. Heterocycl. Comp. in press.
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65(5), 705–727.
JgemZ14.0 Hz, H-60eq), 2.78 (1H, dd, J2 ax3 axZ11.0 Hz,
0
0
J2 ax3 eqZ3.5 Hz, H-20ax), 4.12 (2H, m, CH2CH3), 6.74 (dt,
J78ZJ67Z7.5 Hz, J57Z1.0 Hz, H-7), 6.79 (1H, d, J56Z
8.0 Hz, H-5), 6.86 (1H, broad s, NH), 7.29 (1H, dt, J67Z
J56Z7.8 Hz, J68Z1.5 Hz, H-6), 7.37 (1H, s, SO2NH), 7.45
(1H, dd, J78Z7.8 Hz, J68Z1.3 Hz, H-8). dC(DMSO-d6):
13.82 (CH3CH2), 20.90 (C-50), 23.44 (br, C-40), 25.71
(C-30), 34.01 (br, C-60), 49.72 (br, C-20), 60.76 (CH2CH3),
71.07 (N–C–N), 116.48 (C-5), 117.01 (C-7), 120.30 (C-8a),
123.64 (C-8), 133.15 (C-6), 142.36 (C-4a), 174.32 (br, CO).
0
0
10. (a) Yakimovich, S. I.; Zerova, I. V. Zh. Org. Khim. 1978, 14,
42–48. (b) Yakimovich, S. I.; Zerova, I. V. Zh. Org. Khim.
1978, 14, 266–274. (c) Yakimovich, S. I.; Zerova, I. V.;
Brundina, S. S. Zh. Org. Khim. 1979, 15, 2295–2301. (d)
Yakimovich, S. I.; Zerova, I. V. Zh. Org. Khim. 1993, 29,
905–910.
11. Smith, T. A. K.; Stephen, H. Tetrahedron 1957, 1, 38–44.
12. Bonola, G.; Sianesi, E. Chem. Ber. 1969, 102, 3735–3738.
13. Lessel, J. Arch. Pharm. 1994, 327, 571–579.
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4.2.4.7. 20-Carbethoxy-2H,4H-spiro(benzo-1,2,4-thia-
diazine-3,10-cyclohexane)-1,1-dioxide (23) (axial
carbethoxy group), interpreted signals. dH(DMSO-d6):
1.13 (3H, t, JCH3–CH2Z7.2 Hz, CH3CH2), 1.45–1.85 (4H,
m, cyclohexane ring), 1.76 (1H, m, H-30ax or H-30eq), 1.93
(1H, m, H-30ax or H-30eq), 1.96 (1H, m, H-60eq), 2.29 (1H,
td, J6 ax–5 axZJgemZ13.2 Hz, J6 ax–5 eqZ4.2 Hz, H-60ax),
3.73 (1H, m, H-20eq), 4.06 (2H, m, CH2CH3), 6.70 (1H, dt,
J78ZJ67Z7.5 Hz, J57Z0.6 Hz, H-7), 6.84–6.92 (m, NH,
H-5), 7.25 (1H, dt, J67ZJ56Z7.8 Hz, J68Z1.5 Hz, H-6),
7.44 (1H, dd, J78Z7.8 Hz, J68Z1.3 Hz, H-8). dC(DMSO-
d6): 13.90 (CH3CH2), 20.00 (C-50), 23.44 (br, C-40), 24.36
(C-30), 32.56 (br, C-60), 45.22 (C-20), 59.89 (CH2CH3),
70.70 (N–C–N), 116.29, 116.36 (C-5, C-7), 120.01 (C-8a),
123.47 (C-8), 132.80 (C-6), 142.32 (C-4a), 172.12 (br, CO).
0
0
0
0
17. Jakobsen, P.; Treppendahl, S. Tetrahedron 1979, 35,
2151–2153.
18. Solomko, Z. F.; Fedenko, V. S.; Avramenko, V. I.; Bozhanova,
N.; Ya, . Zh. Org. Khim. 1979, 15, 134–138.
19. Auwers, K.; von Schmidt, W. Ber. 1925, 58, 528–543.
¨
20. Gorlitz, G.; Hartmann, H. Heteroatom Chem. 1997, 8,
147–155.