Abstract
Several structurally differentiated N-alkyl imines were oxidized to their corresponding oxaziridines using UHP/maleic anhydride system. Oxidation reaction was performed under mild conditions and oxaziridines were obtained in good to excellent yields.
Key words
UHP -
N -alkyl imines - oxaziridines
References
1
Davis FA.
Sheppard AC.
J. Org. Chem.
1987,
52:
954
2
Davis FA.
Billmers RH.
J. Am. Chem. Soc.
1981,
103:
7016
3a
Davis FA.
Jenkines RH.
Asymmetric Synthesis: Synthesis and Utilization of Compounds with Chiral Nitrogen Centers
Academic Press, INC.;
New York:
1985.
Chap. 4.
p.313-345
3b
Davis FA.
Sheppard AC.
Tetrahedron
1989,
45:
5703
4
Kidwai M.
Dave B.
Kohli S.
Indian J. Chem.
1999,
38B:
728
5
Davis FA.
Stringer OD.
J. Org. Chem.
1982,
47:
1774
6
Davis FA.
Chattopadhyay S.
Towson JC.
Lal S.
Reddy TR.
J. Org. Chem.
1988,
53:
2087
7a
Kluge R.
Schulz M.
Liebsch S.
Tetrahedron
1996,
52:
5773
7b
Schirmann JP.
Weiss EF.
Tetrahedron Lett.
1972,
633
8a
Martiny L.
Jorgensen KA.
J. Chem. Soc. Perkin Trans. 1
1995,
699
8b
Auret BJ.
Boyd DR.
Coulter PB.
J. Chem. Soc., Chem. Commun.
1984,
463
9
Zolfigol MA.
Bagherzadeh M.
Madrakian E.
Ghaemi E.
Taqian-nasab A.
J. Chem. Res. (S)
2001,
140
10
Zolfigol MA.
Bagherzadeh M.
Chehardoli G.
Mallakpour SE.
Synth. Commun.
2001,
31:
1149
11
Zolfigol MA.
Bagherzadeh M.
Ghorbani Choghamarani A.
Keypour H.
Salehzadeh S.
Synth. Commun.
2001,
31:
1661
12
Zolfigol MA.
Bagherzadeh M.
Chehardoli G.
Mallakpour SE.
Mamaghani M.
J. Chem. Res. (S)
2001,
390
13
Cooper MS.
Heaney H.
Newbold AJ.
Sanderson WR.
Synlett
1990,
533
14
Ballini R.
Marcantoni E.
Petrini M.
Tetrahedron Lett.
1992,
33:
4835
15a
Astodillo L.
Galindo A.
Gonzalez AG.
Mansilla H.
Heterocycles
1993,
36:
1075
15b
Uchida T.
Katsuki T.
Tetrahedron Lett.
2001,
42:
6911
16
Balicki R.
Synth. Commun.
1999,
29:
2235
17
Heaney H.
Newbold AJ.
Tetrahedron Lett.
2001,
42:
6607
18
Perez JM.
Lopez-Alvardo P.
Pascual-Alfonso E.
Avendano C.
Menendez JC.
Tetrahedron
2000,
56:
4575
19
Salandino R.
Carlucci P.
Danti MC.
Crestini C.
Mincione E.
Tetrahedron
2000,
56:
10031
20a
Pietikainen P.
J. Mol. Cat. A: Chem.
2001,
165:
73
20b
Kureshy RI.
Khan NH.
Abdi SHR.
Patel ST.
Jasra RV.
Tetrahedron: Asymmetry
2001,
12:
433
21
Varma RS.
Naicker KP.
Org. Lett.
1999,
1:
189
22
Caron S.
Do NM.
Sieser JE.
Tetrahedron Lett.
2000,
41:
2299
23 Yields refer to isolated pure products. The oxidation products were characterized by comparison of their spectral (IR, 1 H NMR, and 13 C NMR) and physical data with the authentic samples.
24 Oxidation of N -benzylphenyl imine(1a ) to 2-benzyl-3-phenyl oxaziridine(2a ) with UHP/maleic anhydride system. A typical procedure: A suspension of compound 1a (0.390 g, 2 mmol), I (0.188 g, 2 mmol), maleic anhydride (0.176 g, 2 mmol) in methanol (8 mL) was stirred at 0 °C. The progress of the reaction was monitored by TLC (eluent, EtOAc-n -hexane, 1:5). The reaction was completed after 40 min. The reaction mixture was filtered and the filtrate was passed through a short pad of silica gel. Methanol was removed under reduced pressure. Highly pure oxaziridine(2a ) was obtained in 95% yield (0.354 g). (FT-NMR 500 MHz) CDCl3 : δppm 4.03-4.22 (dd, 2 H), 4.8 (s, 1 H), 7.45-7.6 (m, 10 H).
[7a ]
25
Cicchi S.
Marradi M.
Goti A.
Brandi A.
Tetrahedron Lett.
2001,
42:
6503
26
Nakama K.
Seki S.
Kanemasa S.
Tetrahedron Lett.
2001,
42:
6719
27
Long A.
Baldwin SW.
Tetrahedron Lett.
2001,
42:
5343