JOURNAL OF CHEMICAL RESEARCH 2007 277
entry 1) was obtained in 85% yield (0.33 g). IR and 1H NMR spectra
of oxo-compound 6. In the next stage, the imine approaches
oxidant species 6 and an unstable intermediate 7 is formed
that can release oxaziridines or nitrones and regenerated 1.
Comparison of this method for the oxidation of imines with
our previous report24 in terms of amount of catalyst used,
conditions, and yields, show advantages such as catalytic
amount (1%mol for porphyrin compared to 100% for maleic
anhydride system) and shorter reaction times, with retention
of yields, in similar conditions.
1
data confirmed the identities of the product. H NMR (CDCl3)
δ: 7.27–7.97(m, 10H), 8.49(s, 1H). 13C NMR (CDCl3) δ: 160.4,
152.1, 136.3–128.2(6 CH), 120.9(CH). IR (KBr): 3040–2840(sh, s),
1640(s), 1600(s), 1480(s), 1440(s), 1200(s), 760(s), 640(s).
This work was financially supported by the Yasouj University
and Islamic Azad University, Branch of Gachsaran, are
acknowledged.
In conclusion, the results show that the type of the used
metalloporphyrins 1-3 had no important effects on completion
of the reaction. In this paper, we have described a facile, mild
and biomimetic synthesis of oxaziridines and nitrones using
catalytic amounts of metalloporphyrins 1–3 as biological-
model catalysts in the presence of 4 as stable, safe and non-
toxic oxidant. Several advantages of this method including
high yields of products, short reaction times, inexpensive
(catalytic amount of metalloporphyrins 1–3 and non necessity
of axial ligand) and ease of isolation of products, which make
this reaction convenient and efficient.
Received 7 February 2007; accepted 25 May 2007
Paper 07/4465 doi: 10.3184/030823407X215861
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Typical procedure: oxidation of imine (entry 10) to oxaziridine by
metalloporphyrin 1
A suspension of N-benzyl phenyl imine (entry 10, Table 1) (0.39 g,
2 mmol), 4 (0.188 g, 2 mmol), 1 (0.0144 g, 0.02 mmol) in methanol
(10 ml) was stirred at 0°C. The progress of the reaction was monitored
by TLC (n-hexane-ethyl acetate: 80: 20). The reaction was completed
after 15 min. The reaction mixture was filtered and the methanol was
removed under reduced pressure. The residue was purified by a short
pad of silica gel (silica gel 60). Highly pure oxaziridines (Table 1,
entry 10) was obtained in 90% yield (0.38 g). IR and 1H NMR
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13C NMR (CDCl3) δ: 135.8, 134.8, 130.3, 129.8–127.9(5 CH), 80.4,
65.9. IR (KBr): 3040(m), 2960(m), 1490(s), 1450(s), 1400(s), 760(s),
720(s), 690(s).
Typical procedure: oxidation of imine (entry 1) to nitrone by
metalloporphyrin 1
A suspension of N-phenyl phenyl imine (entry 1, Table 1) (0.362 g,
2 mmol), 4 (0.188 g, 2 mmol), 1 (0.0144 g, 0.02 mmol) in methanol
(10 ml) was stirred at 0°C. The progress of the reaction was monitored
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after 10 min. The reaction mixture was filtered and the methanol
was removed under reduced pressure. The residue was purified by
a short pad of silica gel (silica gel 60). Highly pure nitrone (Table 1,
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PAPER: 07/4465