Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane
Publication
, Journal Article
Biswas, KM; Mallik, H; Saha, A; Halder, S; McPhail, AT
Published in: Monatshefte fur Chemie
January 1, 1999
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.
Duke Scholars
Published In
Monatshefte fur Chemie
DOI
ISSN
0026-9247
Publication Date
January 1, 1999
Volume
130
Issue
10
Start / End Page
1227 / 1239
Related Subject Headings
- General Chemistry
- 34 Chemical sciences
- 03 Chemical Sciences
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APA
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Biswas, K. M., Mallik, H., Saha, A., Halder, S., & McPhail, A. T. (1999). Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane. Monatshefte Fur Chemie, 130(10), 1227–1239. https://doi.org/10.1007/PL00010184
Biswas, K. M., H. Mallik, A. Saha, S. Halder, and A. T. McPhail. “Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane.” Monatshefte Fur Chemie 130, no. 10 (January 1, 1999): 1227–39. https://doi.org/10.1007/PL00010184.
Biswas KM, Mallik H, Saha A, Halder S, McPhail AT. Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane. Monatshefte fur Chemie. 1999 Jan 1;130(10):1227–39.
Biswas, K. M., et al. “Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane.” Monatshefte Fur Chemie, vol. 130, no. 10, Jan. 1999, pp. 1227–39. Scopus, doi:10.1007/PL00010184.
Biswas KM, Mallik H, Saha A, Halder S, McPhail AT. Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane. Monatshefte fur Chemie. 1999 Jan 1;130(10):1227–1239.
Published In
Monatshefte fur Chemie
DOI
ISSN
0026-9247
Publication Date
January 1, 1999
Volume
130
Issue
10
Start / End Page
1227 / 1239
Related Subject Headings
- General Chemistry
- 34 Chemical sciences
- 03 Chemical Sciences