Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation of hexakiscarbonylmethyl and hexakiscyanomethyl derivatives of 2,3,6,7,10,11-hexahydroxytriphenylene

Frederik C Krebs, N.C. Schiødt, W. Batsberg Pedersen, K. Bechgaard

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    2,3,6,7,10,11-Hexamethoxytriphenylene (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 giving 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(diethylaminoethyloxy)triphenylene (6) and reduction of 5 followed by acetylation gave 2,3,6,7,10,11-hexakis(acetyloxyethyloxy)triphenylene (7). Hydrolysis of 5 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.
    Original languageEnglish
    JournalSYNTHESIS-STUTTGART
    Issue number11
    Pages (from-to)1285-1290
    ISSN0039-7881
    Publication statusPublished - 1997

    Keywords

    • Triphenylene derivatives
    • purification and synthesis involving peptide coupling strategies

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