A novel method is described for the synthesis of α-oximino-6-acylmethylphenanthridine derivatives (2a–g)B in good to excellent yields based on treatment of 6-acylmethylphenanthridines with isoamyl nitrite (IAN) in DMF without any added acid.
McOmieJ.F.W., Protective Groups in Organic Chemistry, Plenum Press: London and New York, 1973, p. 46.
2.
CameronM., GowenlockB.G., and BoyedA.S.F., J. Chem. Soc. Perkin Trans. 2, 1996, 2271.
3.
VeroneseA.C., VecchiatiG., and OrlandiniP., Synthesis, 1985, 300.
4.
(a) FusonR.G., Reaction of Organic Compounds: a Textbook for the Advanced Student, John Wiley and Sons, Inc.: New York, 1962, p. 535; (b) O. Touster, Org. Reactions, 1953, 7, 327; (c) R.B. Wagner and H.D. Zook, Synthetic Organic Chemistry, John Wiley and Sons, Inc.: New York, 1953, p.739.
5.
KimY.H., ParkY.J., and KimK., Tetrahedron Lett., 1989, 30, 2833.
6.
(a) GrahamA., and WilliamsD.L.H., J. Chem. Soc. Perkin Trans. 2, 1992, 747; (b) E. Iglesias and D.L.H. Williams, J. Chem. Soc. Perkin Trans. 2, 1989, 343; (c) P. Roy and D.L.H. Williams, J. Chem. Res. (S), 1988, 122.
7.
ZolfigolM.A., Molecules, 2001, 6, 694 and references cited therein.
8.
MarchalA., MelguizoM., NoguerasM., SanchezA., and LowJ.N., Synlett.2002, 255.
9.
Loghmani-KhouzaniH., GawineckiR., SadeghiM.M., MehrabiH., and OsmialowskiB., J. Iran. Chem. Soc., 2005, 2, 294.
10.
GilliP., BertolasiV., FerrettiV., and GilliG., J. Am. Chem. Soc., 2000, 122, 10405.
11.
GilliG., BellucciF., FerrettiV., and BertolasiV., J. Am. Chem. Soc., 1989, 111, 1023.
12.
GoldbergN.N., and LevineR., J. Am. Chem. Soc., 1952, 74, 521.
