A novel reductive cyclisation of phenacyl azides brought about by samarium iodide is described in this paper. By this process several 2,4-diarylpyrroles have been prepared.
BogerD.L., BoyceC. W., LabroliM. A., SehonC. A., and JinQ., J. Am. Chem. Soc., 1999, 121, 54.
4.
SundbergR.J., Pyrroles and their benzo derivatives (iii) synthesis and applications, in Comprehensive Heterocyclic Chemistry; A.R. Katritzky and C.W. Rees, Eds., Pergamon, Oxford, 1984; vol. 4, pp. 370–376.
5.
(a) TraceyM.R., HsungR. P., and LambethR. H., Synthesis, 2004, 918 and references therein.
6.
BraunR.U., ZeitlerK.; MullerT. J. J., Org. Lett., 2001, 3, 3297.
7.
BharadwajA.R., and ScheidtK. A., Org. Lett., 2004, 6, 2465.
8.
SundbergR.J., Pyrroles and their benzo derivatives (iii) synthesis and applications, in Comprehensive Heterocyclic Chemistry; KatritzkyA.R., and ReesC. W., Eds., Pergamon, Oxford, 1984; vol. 4, pp. 313–370.
9.
GilchristT.L., J. Chem. Soc., Perkin Trans. 1, 1999, 2849.
10.
GilchristT.L., J. Chem. Soc., Perkin Trans. 1, 1998, 615.
11.
(a) CampiE.M., FallonG. D., JacksonW. R., and NilssonY., Aust. J. Chem., 1992, 45, 1167.
12.
BuchwaldS.L., WannamakerM. W., and WatsonB. T., J. Am. Chem. Soc., 1989, 111, 776.
13.
NittaM., and KobayashiT., Chem. Lett., 1983, 1715.
14.
PadwaA., GruberR., and PashayanD., J. Org. Chem., 1968, 33, 454.
15.
DeadyL.W., Tetrahedron, 1967, 23, 3505.
16.
For reviews see: (a) KriefA., and LavalA. M., Chem. Rev., 1999, 99, 745.
17.
MolanderG.A., Acc. Chem. Res., 1998, 31, 603. (c) G.A. Molander and C.R. Harris, Tetrahedron, 1998, 54, 3321.
18.
MolanderG.A., and HarrisC. R., Chem. Rev., 1996, 96, 307.
Goulaouic-DuboisC., and HesseM., Tetrahedron Lett., 1995, 36, 7427.
21.
(a) MolanderG.A., and HahnG., J. Org. Chem., 1986, 51, 1135.
22.
HanessianS., GirandC., and ChiaraJ. L., Tetrahedron Lett., 1992, 33, 573.
23.
For a preliminary account of these results, see: FanX.S., and ZhangY. M., Tetrahedron Lett., 2002, 43, 1863.
24.
For SmI2-mediated dehalogenation of σ-haloketones or σ-haloesters to give enolates, see: (a) ZhangY.M., LiuT. C., and LinR. H., Synth. Commun., 1988, 18, 2003.
25.
MolanderG.A., and HahnG., J. Org. Chem., 1986, 51, 1135.
26.
BoyerJ.H., and StrawD. J., J. Am. Chem. Soc., 1953, 75, 1642.