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Synthesis 1997; 1997(11): 1285-1290
DOI: 10.1055/s-1997-3188
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Purification of 2,3,6,7,10,11-Hexamtheoxytriphenylene and Preparation of Hexakiscarbonylmethyl and Hexakiscyanomethyl Derivatives of 2,3,6,7,10,11-Hexahydroxytriphenylene

Frederik C. Krebs, Niels C. Schiødt, Walther Batsberg, Klaus Bechgaard*
  • *Macromolecular Chemistry Group, Condensed Matter Physics and Chemistry Department, Risø National Laboratory, DK-4000 Roskilde, Denmark
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Publication Date:
31 December 2000 (online)

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2,3,6,7,10,11-Hexahydroxytriphenylene (1) was subjected to an improved purification procedure and demethylated to give 2,3,6,7,10,11-hexahydroxytriphenylene (2) as the relatively stable trihydrate. Compound 2 was alkylated with reactive halogen reagents given 2,3,6,7,10,11-hexakis(cyanomethyl)triphenylene (3), 2,3,6,7,10,11-hexakis(N,N-diethylcarbamoylmethyloxy)triphenylene (4) and 2,3,6,7,10,11-hexakis(ethoxycarbonylmethyloxy)triphenylene (5). Reduction of 4 gave 2,3,6,7,10,11-hexakis(diethyl-aminoethyloxy)triphenylene (6) and reduction of 5 followed by acetylation gave 2,3,6,7,10,11-hexakis(carboxymethyloxy)triphenylene (8). Compound 8 could be converted to its corresponding active N-hydroxysuccinimide ester (9) by the DCC method. Compound 9 was found to be a versatile core molecule that could be coupled with glycine-t-butyl ester, L-phenylalanine and L-phenylalanine-t-butyl ester giving compounds 10, 11 and 12.

triphenylene derivatives - purification and synthesis involving peptide coupling strategies

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