Synthesis and Reactions of Oxazolones from L‑Tryptophan and α‑Haloacetic Anhydrides
1992 (English)In: Bulletin des Sociétés chimiques belges, ISSN 0037-9646, Vol. 101, no 7, 643-660 p.Article in journal (Refereed) Published
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.
IdentifiersURN: urn:nbn:se:uu:diva-140716DOI: 10.1002/bscb.19921010712ISI: A1992JM80900011OAI: oai:DiVA.org:uu-140716DiVA: diva2:384254