DOI QR코드

DOI QR Code

Chemistry of the 3a,7a-Dihydro-1H-indole Esters. Aromatization by Bromine$^\dag$

  • Lee, Chang-Kiu (Department of Chemistry, Kangweon National University) ;
  • Ahn, Yu-Mi (Department of Chemistry, Kangweon National University) ;
  • Han Lee, In-Sook (Department of Science Education, Kangweon National University)
  • Published : 1986.08.20

Abstract

A series of tetramethyl 1-substituted benzyl-3a,7a-dihydro-1H-indole-2,3,3a,4-tetracarboxylates were prepared and their reactions with bromine were examined. The initial reaction seemed to be the formation of the intermediate N-bromo quaternary ammonium bromide. This intermediate underwent aromatization with loss of the 3a-methoxycarbonyl group. Bromine replaced the N-substituent of the p-methoxybenzyl compound and addition of bromine occurred across the $C_6-C_7$ double bond of the indole ring. Bromination of the benzyl ring and aromatization occurred for the m-methoxybenzyl compound.

Keywords

References

  1. J. Am. Chem. Soc. v.75 Steck, E.A.;Brundage, R. P.;Feltcher, L. T.
  2. J. Chem. Rev. v.72 Eisner, U.;Kuthan
  3. Chem. Ind. Tamura, Y.;Yoshimoto, Y.
  4. J. Org. Chem. v.43 Lee, C. K.;Hahn, C. S.;Noland, W. E.
  5. J. Org. Chem. v.45 Noland, W.E.;Lee, C.K.
  6. Acta Chem. Scand. v.6 Elming, N.;Clauson-Kass, N.
  7. J. Chem. Soc. Acheson, R.M.;Vernon, J.M.
  8. Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry Jackman, L.M.;Sternhell, S.