The reaction of 2,3,4,9-tetrahydro-1H-carbazol-1-ones with ethyl acetate yielded 2-acetyl-1-hydroxycarbazole and 2-acetyl-2,3,4,9-tetrahydro-1H-carbazol-1-one. These were used to prepare isoxazolo- and pyrazolo-fused carbazoles. Mechanisms for the formation of the end products are proposed.
MalD., SenapatiB., and PahariP., Tetrahedron Lett., 2006, 47, 1071.
2.
PindurU., Chimia, 1990, 44, 406.
3.
KnolkerH.J., and ReddyK.R., Chem. Rev., 2002, 102, 4303.
4.
HewlinsM.J.E., CamposA.M.O., and ShannonP.V.R., Synthesis, 1984, 289.
5.
GribbleG.W., The Alkaloids, ed. BrossiA., Academic Press, New York1990, Vol. 39, 239–241.
6.
KansalV.K., and PotierP., Tetrahedron, 1986, 32, 2389.
7.
HaiderN., JabaraR., KhadamiF., and WankoR., Heterocycles, 1998, 48, 1609.
8.
HedinV.M., TabkaT., PoulinL., GodardT., LachevrelM., SaturninoC., LancelotJ.C., Le TalaerJ.Y., and GauduchonP., Anti Cancer Drug Design, 2000, 15, 109.
9.
HirataK., ItoC., FurukawaH., ItoigawaM., Mark CosentinoL., and LeeK.H., Bioorg. Med. Chem. Lett., 1999, 9, 119.
10.
IshikuraM., HinoA., YaginumaT., AgataI., and KatagiriN., Tetrahedron, 2000, 56, 193.
11.
ThomasK.R.J., LinJ.T., TaoY.T., and KoC.W., J. Am. Chem. Soc., 2001, 123, 9404.
12.
Van DijkenA., BastiaansenJ.A.M., KiggenN.M.M., LangeveldB.M.W., RotheC., MonkmanA., BachI., StoesselP., and BrunnerK., J. Am. Chem. Soc., 2004, 126, 7718.
13.
ChmielewskiM.J., CharonM., and JurczakJ., Org. Lett., 2004, 6, 3501.
14.
Vandana, and Rajendra PrasadK.J., J. Chem. Res., 2004, 717.
15.
ThiruvalluvarA., Thomas GunaseelanA., Ebenezer MartinA., Rajendra PrasadK.J., and ButcherR.J., Acta Cryst.2007, E63, o3631.
16.
Ebenezer MartinA., Thomas GunaseelanA., ThiruvalluvarA., Rajendra PrasadK.J., and ButcherR.J., Acta Cryst.2007, E63, o3471.