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For the synthesis and application
of this and related compounds see:
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5
A representative
procedure for the preparation is as follows:
Preparation
of Dimethyl 2-[(methoxycarbonyl)amino]-6-benzoyl-3-methyl-2,6-diazabicyclo [3.1.0] hex-3-ene-4,5-dicarboxylate 3a. 1,2-Diaza-1,3-butadiene 1a (1
mmol) and methyl 2-benzoylamino-3-dimethylamino-propenoate 2 (1 mmol) were dissolved in 30 mL of toluene
and refluxed until the reaction was complete (monitored by TLC).
The reaction mixture was concentrated directly under reduced pressure and
product 3a was isolated by chromatography
on silica, eluting with cycloexane-ethyl acetate (70:30)
and then purified by crystallization from diethyl ether.
3a: mp 106-110 °C; IR(nujol)
3287, 2765, 1704, 1658
cm-1; 1H
NMR (DMSO-d
6) δ 2.07
(s, 3 H, CH3), 3.60 (s, 3 H, OCH3), 3.66 (s,
3 H, OCH3), 6.17 (s, 1 H, CH), 7.45-7.91 (m,
5 Har), 9.94 (b.s., 1 H, NH); 13C
NMR (DMSO-d
6) δ 11.3 (CH3),
50.6 (OCH3), 52.5 (OCH3), 83.8 (C5), 98.2
(C1), 100.7 (C4), 126.0 (Car), 128.1 (Car),
128.5 (Car), 132.1 (Car), 156.0 (C3), 161.5
(CO), 163.3 (CO), 163.8 (CO), 169.4 (CO) MS m/z 389 (M+, 76), 360(32),
330(88), 254(32), 222(35), 167(100). Anal.Calcd for C18H19N3O7:
C, 55.53; H, 4.92; N, 10.79. Found: C, 55.45; H, 4.98; N, 10.66.
6a
Kumar PR.
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Kumar PR.
Heterocycles
1987,
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7
Jones DW.
J.
Chem. Soc. D.
1971,
18:
1130
8
Fischer U.
Schneider F.
Helv. Chim. Acta
1980,
63:
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