5822
V. P. Sheverdov et al. / Tetrahedron 57 /2001) 5815±5824
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Ê 3
b7.65482) A, c14.72582) A, a97.6382)8, b93.2482)8,
1.6.25. 5-Hydroxy-3-*4-methoxyphenyl)-7-oxo-4-propyl-
6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitrile *8d). 83.53 g,
97%) as a colorless solid, mp 185±1868decomp.)8C;
[Found: C, 65.8; H, 5.5; N, 15.2. C20H20N4O3 requires C,
65.92; H, 5.53; N, 15.38%]; nmax8Nujol) 3510, 3350, 2275,
1710, 1645 cm21; dH 8300 MHz, DMSO) 9.54 81H, s, NH),
7.51 82H, d, J8.5 Hz, o-Ph), 7.12 82H, d, J8.5 Hz, m-Ph),
7.09 81H, s, OH), 3.84 83H, s, OCH3), 3.79 81H, d, 12.5,
CHAr), 3.74 81H, d, J14.5 Hz, CH2), 3.37 81H, d,
J12.5 Hz, CHPr), 3.26 81H, d, J14.5 Hz, CH2), 1.5±
1.1 84H, m, CH2CH2CH3), 0.82 83H, t, J6.5 Hz,
CH2CH2CH3).
g109.9082)8, V637.083) A , dcalcd1.270 g cm23, Z
2. The space group is P21/c. Summary of Data CCDC
153640.
1.6.20. 1,2,2-Tricyano-3-*2-furyl)-5-oxo-1-cyclohexane-
carboxamide *7g). 80.27 g, 95%) as a colorless solid,
mp 170±1718decomp.)8C; [Found: C, 59.7; H, 3.4; N,
19.8. C14H10N4O3 requires C, 59.57; H, 3.57; N, 19.85%];
n
max8Nujol) 3275, 3380, 2275, 1705, 1740 cm21; dH
8300 MHz, DMSO) 7.94 81H, d, J1.5 Hz, Fu), 6.79 81H,
d, J3.0 Hz, Fu), 6.68 81H, dd, J3.0, 1.5 Hz, Fu), 6.56
81H, s, CONH2), 6.51 81H, s, CONH2), 3.83 81H, dd,
J12.0, 4.5 Hz, CHFu), 2.98 81H, d, J14.5 Hz,
1.6.26. 5-Hydroxy-3-*4-methoxyphenyl)-4,8-dimethyl-7-
oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitrile *8e).
CH2C8CN)CONH2),
2.56
81H,
d,
J14.5 Hz,
CH2C8CN)CONH2), 2.28 81H, dd, J14.5, 12.0 Hz,
83.27 g, 98%) as
a
colorless solid, mp 1176±
CH2CHFu), 2.20 81H, dd, J14.5, 4.5 Hz, CH2CHFu).
11778decomp.)8C; [Found: C, 65.1 H, 5.1; N, 16.0.
C19H18N4O3 requires C, 65.13; H, 5.53; N, 15.99%]; nmax8-
Nujol) 3485, 3350, 2265, 1720, 1640 cm21; dH 8300 MHz,
DMSO) 9.48 81H, s, NH), 7.45 82H, d, J8.5 Hz, o-Ph),
7.05 82H, d, J8.5 Hz, m-Ph), 7.02 81H, s, OH), 3.84 83H,
s, OCH3), 3.76 81H, d, J12.0 Hz, CHAr), 3.08 81H, q,
J7.0 Hz, CHCH3), 2.84 81H, m, ArCHCHCH3), 1.34
83H, d, J7.0 Hz, CHCH3), 0.96 83H, d, J6.5 Hz,
CHCH3).
1.6.21. 1,2,2-Tricyano-3-isopropyl-5-oxo-1-cyclohexane-
carboxamide *7h). 80.24 g, 92%) as a colorless solid,
mp 180±1818decomp.)8C; [Found: C, 60.5; H, 5.3; N,
21.7. C13H14N4O2 requires C, 60.46; H, 5.46; N, 21.69%];
n
max8Nujol) 3260, 3380, 2260, 1710, 1730 cm21; dH
8300 MHz, DMSO) 6.58 81H, s, CONH2), 6.52 81H, s,
CONH2), 2.86 81H, d, J14.0 Hz, COCH2), 2.43 81H, d,
J14.0 Hz, COCH2), 2.25 81H, m, CHMe2), 2.2 8d, 1H,
COCH2), 2.04 81H, d, J14.5, 11.0 Hz, CHCH2), 1.58
81H, dd, J14.5, 3.5 Hz, CHCH2), 1.15 83H, d, J6.5 Hz,
CHMe2), 1.09 83H, d, J6.5 Hz, CHMe2).
1.6.27. 5-Hydroxy-8-isopropyl-3-*4-methoxyphenyl)-7-
oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitrile *8f).
83.5 g, 96%) as a colorless solid, mp 187±1888decomp.)8C;
[Found: C, 65.9; H, 5.5; N, 15.3. C20H20N4O3 requires C,
65.92; H, 5.53; N, 15.38%]; nmax8Nujol) 3505, 3350, 2270,
1710, 1640 cm21; dH 8300 MHz, DMSO) 9.50 81H, s, NH),
7.4 82H, d, J8.5 Hz, o-Ph), 7.02 82H, d, J8.5 Hz, m-Ph),
7.06 81H, s, OH), 3.9 81H, dd, J12.0, 4.0 Hz, CHAr), 3.84
83H, s, OCH3), 3.55 81H, d, J6.0 Hz, CHCOH), 3.52 81H,
dd, J14.0, 12.0 Hz, CH2), 2.66 81H, dd, J14.0, 4.0 Hz,
CH2), 2.52 81H, m, CHMe2), 1.54 83H, d, J7.0 Hz, CH3),
1.02 83H, d, J6.5 Hz, CH3).
1.6.22. 5-Hydroxy-3-methyl-7-oxo-4-propyl-6-azabicyclo-
[3.2.1]octane-1,2,2-tricarbonitrile *8a). 82.48 g, 90%) as a
colorless solid, mp 114±1158C; [Found: C, 61.6; H, 5.8; N,
20.7. C14H16N4O2 requires C, 61.75; H, 5.92; N, 20.58%];
n
max8Nujol) 3470, 3325, 2275, 1710, 1655 cm21; dH
8300 MHz, DMSO) 9.51 81H, s, NH), 7.82 81H, s, OH),
2.67 81H, d, J13.0 Hz, CH2), 2.42 81H, d, J13.0 Hz,
CH2), 2.61 81H, dt, J12.5, 5.5 Hz, CHPr), 2.55 81H, m,
CH3CH), 1.62 82H, m, CH2CH2CH3), 1.55 83H, d, J
6.5 Hz, CHCH3), 1.32 82H, m, CH2CH2CH3), 1.21 8m, 1H,
CH2CH2CH3), 0.91 83H, t, J6.0 Hz, CH2CH2CH3).
1.6.28. 3-*2-Furyl)-5-hydroxy-7-oxo-6-azabicyclo[3.2.1]-
octane-1,2,2-tricarbonitrile *8g). 82.65 g, 94%) as a color-
less solid, mp 206±2078decomp.)8C; [Found: C, 59.7; H,
3.5; N, 19.8. C14H10N4O3 requires C, 59.57; H, 3.57; N,
1.6.23. 5-Hydroxy-7-oxo-3,4-dipropyl-6-azabicyclo[3.2.1]-
octane-1,2,2-tricarbonitrile *8b). 82.67 g, 89%) as a color-
less solid, mp 110±1118C; [Found: C, 64.1; H, 6.8; N,
18.5. C16H20N4O2 requires C, 63.98; H, 6.71; N, 18.65%];
19.85%]; nmax8Nujol) 3510, 3370, 2265, 1725, 1605 cm21
;
dH 8300 MHz, DMSO) 9.45 81H, s, NH), 7.92 81H, d, J
2.0 Hz, Fu), 7.25 81H, s, OH), 6.72 81H, d, J3.0 Hz, Fu),
6.58 81H, dd, J2.0, 3.0 Hz, Fu), 3.73 81H, dd, J12.0,
5.0 Hz, CHFu), 2.89 81H, d, J12.5 Hz, CH2CCN), 2.55
81H, d, J12.5 Hz, CH2CCN), 2.28 81H, t, J12.0 Hz,
CH2CH), 2.25 81H, dd, J12.0, 5.0 Hz, CH2CH).
n
max8Nujol) 3475, 3340, 2275, 1720, 1655 cm21; dH
8300 MHz, DMSO) 9.57 81H, s, NH), 7.85 81H, s, OH),
2.73 81H, d, J12.5 Hz, CH2), 2.38 81H, d, J12.5 Hz,
CH2), 1.1±1.9 810H, m, CHPr, CH2CH2CH3), 1.03 83H, t,
J7.0 Hz, CH2CH3), 0.9 83H, t, J7.0 Hz, CH2CH3).
1.6.29. 5-Hydroxy-3-isopropyl-7-oxo-6-azabicyclo[3.2.1]-
octane-1,2,2-tricarbonitrile *8h). 81.78 g, 69%) as a color-
less solid, mp 175±1768C; [Found: C, 60.3; H, 5.5; N,
19.2. C13H14N4O2 requires C, 60.46; H, 5.46; N, 21.69%];
1.6.24. 5-Hydroxy-7-oxo-3-phenyl-4-propyl-6-azabicyclo-
[3.2.1]octane-1,2,2-tricarbonitrile *8c). 83.27 g, 98%) as a
colorless solid, mp 211±2128decomp.)8C; [Found: C, 68.5;
H, 5.6; N, 16.5. C19H18N4O2 requires C, 68.25; H, 5.43; N,
n
max8Nujol) 3490, 3295, 2270, 1700, 1610 cm21; dH
16.76%]; nmax8Nujol) 3535, 3335, 2270, 1710, 1645 cm21
;
8300 MHz, DMSO) 9.22 81H, s, NH), 7.0 81H, s, OH), 2.7
81H, d, J12.5 Hz, CH2CCN), 2.35 81H, d, J12.5 Hz,
CH2CCN), 1.9±2.17 83H, m, CHCH2, CHCH2, Me2CH),
1.65 81H, m, CHCH2), 1.13 83H, d, J6.5 Hz, CHCH3),
1.1 83H, d, J6.5 Hz, CHCH3). Crystal data for 8h:
C13H14N4O2, M258.35, crystals are triclinic, at 29382)
dH 8300 MHz, DMSO) 9.65 81H, s, NH), 7.4±7.6 85H, m,
Ph), 6.97 81H, s, OH), 3.05 81H, d, J11.5 Hz, CHPh), 2.85
81H, d, J12.0 Hz, CH2), 2.72 81H, d, J12.0 Hz, CH2),
2.43 81H, dt, J11.5, 6.5 Hz, CHPr), 1.5 81H, m, CH2Et),
1.3 81H, m, CH2Et), 1.08 81H, m, CH2CH2CH3), 0.87 81H,
m, CH2CH2CH3), 0.65 83H, t, J7.5 Hz, CH2CH3).
Ê
Ê
Ê
K a7.1370810) A, b8.9260810) A, c12.3780810) A,