1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES
679
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(3aR,6R,6aS)-( )-5-Benzyl-2,6-diphenylper-
hydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIIa).
mp 278 280 C (from Et2O CH2Cl2). IR spectrum
1050 w, 1045 w. H NMR spectrum (CDCl3), , ppm:
2.79 s (3H, CH3), 3.49 d (1H, 6a-H, J = 7.7 Hz),
4.04 d (1H, 3a-H, J = 7.7 Hz), 4.94 s (1H, 6-H), 7.2
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7.5 m (5H, Harom). 13C NMR spectrum (CDCl3),
,
(CHCl3), , cm : 3070 br.w, 2935 w, 1785 w,
ppm: 28.7 (CH3); 47.2, 47.9 (C3a, C6a); 64.3 (C6C);
125.6, 125.9, 128.5, 128.7, 128.8, 129.3, 131.0, 138.3
(Carom); 165.4, 169.4, 175.1 (CO). Found, %: C 71.40;
H 4.97; N 8.78. C19H16N2O3. Calculated, %: C 71.24;
H 5.03; N 8.74.
1725 s, 1700, 1600 w, 1505, 1460 w, 1430, 1375,
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1090 w, 1035 w. H NMR spectrum (CDCl3), , ppm:
3.55 d (1H, CH2, J = 14.5 Hz), 3.88 d.d (1H, 6a-H,
J = 9.4, 10.2 Hz), 4.02 d (1H, 3a-H, J = 9.4 Hz),
4.89 d (1H, 6-H, J = 10.2 Hz), 5.24 d (1H, CH2, J =
14.5 Hz), 6.8 7.5 m (15H, Harom). 13C NMR spectrum
(CDCl3), C, ppm: 41.1 (C6a); 45.1 (CH2); 49.0 (C3a);
61.0 (C6); 125.6, 127.9, 128.3, 128.6, 128.7, 129.0,
129.1, 130.9, 134.3, 134.5 (Carom); 165.5, 169.4,
172.2 (CO). Found, %: C 75.85; H 5.16; N 7.18.
C25H20N2O3. Calculated, %: C 75.74; H 5.08; N 7.07.
(3aR,6S,6aS)-( )-2-Ethyl-5-isopropyl-6-phenyl-
perhydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIe).
mp 136 138 C (from Et2O). IR spectrum (CHCl3), ,
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cm : 3040 br.w, 2985 w, 2940 w, 2880 w, 1780,
1710 s, 1600 w, 1460 w, 1445 w, 1420, 1400, 1380,
1350, 1280 w, 1255 w, 1135. 1H NMR spectrum
(CDCl3), , ppm: 0.83 d (3H, CH3, J = 6.6 Hz),
1.15 d (3H, CH3, J = 6.6 Hz), 1.15 t (3H, CH3, J =
7.1 Hz), 3.22 d (1H, 6a-H, J = 7.9 Hz), 3.57 q (2H,
CH2, J = 7.1 Hz), 3.91 d (1H, 3a-H, J = 7.9 Hz),
4.12 quint (1H, CH, J = 6.6 Hz), 4.98 s (1H, 6-H),
7.2 7.5 m (5H, Harom). 13C NMR spectrum (CDCl3),
, ppm: 12.5, 19.5, 20.3 (CH3); 33.9 (CH2); 45.6,
48.1, 48.5 (C3a, C6a, CHN); 60.5 (C6); 125.6, 128.4,
128.9, 141.0 (Carom); 165.3, 170.4, 175.9 (CO).
Found, %: C 67.91; H 6.77; N 9.37. C17H20N2O3.
Calculated, %: C 67.98; H 6.71; N 9.33.
(3aR,6S,6aS)-( )-2-Ethyl-5-methyl-6-phenylper-
hydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIb).
mp 143 144 C (from Et2O). IR spectrum (CHCl3), ,
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cm : 3040 w, 2985 w, 2940 w, 2885 w, 1780,
1720 s, 1460 w, 1390, 1380, 1350, 1250 w, 1135 w.
1H NMR spectrum (CDCl3), , ppm: 1.18 t (3H,
CH3C, J = 7.3 Hz), 2.74 s (3H, CH3N), 3.31 d.d
(1H, 6a-H, J = 1.3, 8.4 Hz), 3.59 q (2H, CH2, J =
7.3 Hz), 3.88 d (1H, 3a-H, J = 8.4 Hz), 4.83 d (1H,
6-H, J = 1.3 Hz), 7.2 7.5 m (5H, Harom). 13C NMR
spectrum (CDCl3), C, ppm: 12.6 (CH3C); 28.5
(CH3N); 34.1 (CH2); 47.0, 47.8 (C3a, C6a); 64.1 (C6);
125.5, 128.6, 129.2, 138.4 (Carom); 165.6, 170.2,
175.8 (CO). Found, %: 66.23; H 5.97; N 10.13.
C15H16N2O3. Calculated, %: C 66.16; H 5.92;
N 10.29.
(3aR,6R,6aS)-( )-2-Ethyl-5-isopropyl-6-phenyl-
perhydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIIe).
mp 154 155 C (from Et2O CH2Cl2). IR spectrum
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(CHCl3), , cm : 3040 br, 2985, 2945 w, 2880 w,
1780, 1715 s, 1460, 1445, 1425, 1395, 1380, 1345,
1280, 1130, 1080 w, 1040 w, 940 w. H NMR spec-
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(3aR,6R,6aS)-( )-2-Ethyl-5-methyl-6-phenylper-
hydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIIb).
mp 162 163 C (from Et2O). IR spectrum (CHCl3), ,
trum (acetone-d6), , ppm: 0.90 t (3H, CH3, J =
7.1 Hz), 0.99 d (3H, CH3, J = 7.1 Hz), 1.24 d (3H,
CH3, J = 6.6 Hz), 3.22 m (2H, CH2), 3.74 d.q (1H,
CH, J = 6.6, 7.1 Hz), 3.78 d (1H, 3a-H, J = 9.3 Hz),
3.95 d.d (1H, 6a-H, J = 9.3, 10.6 Hz), 5.27 d (1H,
6-H, J = 10.6 Hz), 7.0 7.4 m (5H, Harom). 13C NMR
spectrum (CDCl3), C, ppm: 12.1, 19.0, 20.1 (CH3);
33.7 (CH2); 43.4, 46.6, 49.4 (C3a, C6a, CHN); 61.3
(C6); 125.1, 128.1, 128.4, 128.7, 136.7 (Carom); 165.7,
170.7, 173.2 (CO). Found, %: C 67.73; H 6.99;
N 9.21. C17H20N2O3. Calculated, %: C 67.98; H 6.71;
N 9.33.
(3aR,6S,6aR)-( )-3a-Bromodifluoromethyl-2-
ethyl-5-isopropyl-6-phenylperhydropyrrolo[3,4-c]-
pyrrole-1,3,4-trione (XIIIe). mp 111 113 C (from
Et2O hexane). IR spectrum (CHCl3), , cm :
3040 br, 2985, 2940 w, 2885 w, 1790, 1730 s, 1460,
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cm : 3035 w, 2985 w, 2940 w, 2880 w, 1780, 1720 s,
1460 w, 1395, 1380, 1350, 1280 w, 1140 w, 1120 w,
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1105 w, 1075 w. H NMR spectrum (acetone-d6), ,
ppm: 0.87 t (3H, CH3, J = 7.1 Hz), 2.59 m (1H, CH2),
2.64 s (3H, CH3), 3.23 m (2H, CH2), 3.82 d (1H,
3a-H, J = 9.3 Hz), 3.98 d.d (1H, 6a-H, J = 9.3,
10.6 Hz), 5.12 d (1H, 6-H, J = 10.6 Hz), 7.1 7.4 m
(5H, Harom). 13C NMR spectrum (CDCl3), C, ppm:
12.2 (CH3C); 28.9 (CH3N); 33.8 (CH2); 43.0, 48.8
(C3a, C6a); 63.9 (C6); 126.7, 128.7, 128.9, 134.6
(Carom); 166.1, 170.4, 173.1 (CO). Found, %: C 66.11;
H 5.89; N 10.49. C15H16N2O3. Calculated, %:
C 66.16; H 5.92; N 10.29.
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(3aR,6S,6aS)-( )-5-Methyl-2,6-diphenylper-
hydropyrrolo[3,4-c]pyrrole-1,3,4-trione (XIc).
mp 163 167 C (from Et2O). IR spectrum (CHCl3), ,
1445, 1425, 1395, 1380, 1350, 1340, 1280, 1240,
1160, 1120, 1080, 1060, 960 w. H NMR spectrum
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cm : 3050 w, 2980 w, 2930 w, 1785 w, 1725 s,
1600 w, 1505 w, 1460 w, 1380, 1105 w, 1085 w,
(CDCl3), , ppm: 1.03 t (3H, CH3, J = 7.0 Hz), 1.11 d
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 5 2002