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Synlett 2000; 2000(5): 0647-0649
DOI: 10.1055/s-2000-6603
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Synthesis of 2-Acyl- and 2-Ethoxycarbonyl-3-alkylindoles from o-Alkynyltrifluoroacetanilides

Antonio Arcadi* , Sandro Cacchi, Giancarlo Fabrizi, Fabio Marinelli
  • *Dipartimento di Chimica, Ingegneria Chimica e Materiali della Facoltà di Scienze, Università de L'Aquila, Via Vetoio, Coppito Due, I-57100 L'Aquila, Italy; Fax + 39-06-49912780; E-mail: cacchi@uniroma1.it
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Publication Date:
31 December 2000 (online)

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The reaction of readily available o-alkynyltrifluoroacetanilides with ethyl iodoacetate, ethyl bromoacetate or α-bromoketones in the presence of K2CO3 affords 2-ethoxycarbonyl- and 2-acyl-3-alkylindoles in good to high yield. The synthesis proceeds via an in situ sequential alkylation-cyclization process.

2-alkoxycarbonylindoles - 2-acylindoles - cyclization - alkynes