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Synthesis and Reactions of Oxazolones from L‑Tryptophan and α‑Haloacetic Anhydrides
CNT, DEPT ORGAN CHEM, S-14157 HUDDINGE, SWEDEN .
ROYAL INST TECHNOL, DEPT ORGAN CHEM, S-10044 STOCKHOLM 70, SWEDEN.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
1992 (English)In: Bulletin des Sociétés chimiques belges, ISSN 0037-9646, Vol. 101, no 7, 643-660 p.Article in journal (Refereed) Published
Abstract [en]

Optically active 5(4H)-oxazolones have been synthesized from L-tryptophan and an excess of trifluoro-, trichloro-, and dichloroacetic anhydrides. Some of the 5(4H)-xazolones have been further transformed to the isomeric 5(2H)-oxazolones as well as oxazolones with exocyclic double bonds. Treatment of the various oxazolones under hydrolytic, acidic and Friedel-Crafts acylation conditions gave indole-3-pyruvic acid, alpha,beta-dehydrotryptophans, beta-carbolines as well as the functionalized cyclopentanoindole 32. Treatment of the 4-(3-indolylmethyl)-2-trifluoromethyl-5(2H)-oxazolone (17) with trifluoroacetic acid gave the 3,4-bridged azepinoindole 35.

Place, publisher, year, edition, pages
1992. Vol. 101, no 7, 643-660 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-140716DOI: 10.1002/bscb.19921010712ISI: A1992JM80900011OAI: oai:DiVA.org:uu-140716DiVA: diva2:384254
Available from: 2011-01-08 Created: 2011-01-08 Last updated: 2011-03-08Bibliographically approved

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Gogoll, Adolf

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