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Paper | Regular issue | Vol 27, No. 6, 1988, pp.1365-1376
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4453
The Formation of Substituted Indoles by Acid Catalyzed Rearrangements of 4-Isoxazolines

Angelo Liguori, Rosaria Ottana, Giovanni Romeo,* Giovanni Sindona, and Nicola Uccella

*Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy


Thermal rearrangements of 4-isoxazolines from C,N-diphenylnitrone and substituted alkynes have been directed towards the formation of substituted indoles. Detection and isolation of the intermediates of the process elucidate the reaction pathway. The appropriate choice of substituents and experimental conditions has allowed the control of the single steps involved in the total process.