Summary.
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.
Zusammenfassung.
5,11-Dihydro-5,11-dibenzyl-6-trifluormethylindolo[3,2-b]carbazol (6) und das cyclische N-Benzylindoltrimer 4 wurden aus N-Benzylindol-3-methanol (1) und N,N′-Dibenzyl-3,3′-diindolylmethan (2) durch Behandeln mit Trifluoracetanhydrid synthetisiert. Ersteres ergab auch das36-gliedrige cyclische N-Benzylindoltetramer 7, letzteres N-Benzyl-3-trifluoracetylindol (8). Erhitzen von 1 in wässrigem Methanol führte zum Trimer 4– zusammen mit 2, dem N-Benzyltriindolylmethan 3 und dem N-Benzyl-tetraindolyltrimethan 5, für welches Struktur und Konformation imfesten Zustand durch Röntgenstrukturanalyse abgeleitet wurden. Die Resultate werden diskutiert, und plausible Mechanismen für die Reaktionen, die zu den Verbindungen 3–8 führen, werden vorgestellt.
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Received January 28, 1999. Accepted February 16, 1999
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Biswas, K., Mallik, H., Saha, A. et al. Synthesis of a Trifluoromethylindolocarbazole, Novel Cyclic 27- and 36-Membered N-Benzyltri- and -tetraindoles, and an N-Benzyltetraindolyltrimethane. Monatshefte fuer Chemie 130, 1227–1239 (1999). https://doi.org/10.1007/PL00010184
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DOI: https://doi.org/10.1007/PL00010184