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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 universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
1992 (engelsk)Inngår i: Bulletin des Sociétés chimiques belges, ISSN 0037-9646, Vol. 101, nr 7, s. 643-660Artikkel i tidsskrift (Fagfellevurdert) 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.

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1992. Vol. 101, nr 7, s. 643-660
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URN: urn:nbn:se:uu:diva-140716DOI: 10.1002/bscb.19921010712ISI: A1992JM80900011OAI: oai:DiVA.org:uu-140716DiVA, id: diva2:384254
Tilgjengelig fra: 2011-01-08 Laget: 2011-01-08 Sist oppdatert: 2011-03-08bibliografisk kontrollert

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