Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane


Journal Article

5,11-Dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole (6) and the cyclic N-benzylindole trimer 4 were synthesized from both N-benzylindole-3-methanol (1) and N,N'-dibenzyl-3,3'-diindolylmethane (2) by treatment with trifluoroacetic anhydride. The former also gave the 36-membered cyclic N-benzylindole tetramer 7, and the latter furnished N-benzyl-3-trifluoroacetylindole (8). Heating 1 in aqueous methanol also yielded the trimer 4 along with 2, the N-benzylitriindolyldimethane 3, and the N-benzyltetraindolyltrimethane 5 whose structure and solid-state conformation were determined by X-ray crystallographic analysis. The results are discussed and plausible mechanisms of the reactions leading to 3-8 are presented.

Full Text

Duke Authors

Cited Authors

  • Biswas, KM; Mallik, H; Saha, A; Halder, S; McPhail, AT

Published Date

  • January 1, 1999

Published In

Volume / Issue

  • 130 / 10

Start / End Page

  • 1227 - 1239

International Standard Serial Number (ISSN)

  • 0026-9247

Digital Object Identifier (DOI)

  • 10.1007/PL00010184

Citation Source

  • Scopus