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DOI: 10.1055/s-2003-39286
Simple and Convenient Preparation of New Highly Protected Aziridines Fused with Pyrroline Rings
Publication History
Publication Date:
20 May 2003 (online)
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Abstract
New highly protected aziridines fused with pyrroline rings are obtained in satisfactory yields by reaction of 1,2-diaza-1,3-butadienes with methyl 2-benzoylamino-3-dimethylamino-propenoate in toluene under reflux.
Key words
Michael additions - regioselectivity - bicyclic compounds - 1,2-diaza-1,3-butadienes - aziridines
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References
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.