Useful Access to Uncommon Thiazolo[3,2-]indoles.

Giacomo Mari, Lucia De Crescentini, Gianfranco Favi, Amalija Golobič, Stefania Santeusanio, Fabio Mantellini
Author Information
  1. Giacomo Mari: Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino (PU), Italy. ORCID
  2. Lucia De Crescentini: Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino (PU), Italy. ORCID
  3. Gianfranco Favi: Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino (PU), Italy. ORCID
  4. Amalija Golobič: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia.
  5. Stefania Santeusanio: Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino (PU), Italy. ORCID
  6. Fabio Mantellini: Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino (PU), Italy. ORCID

Abstract

A practical and environmentally benign protocol for the assembly of poly substituted-thiazolo[3,2-]indoles from 3-alkylated indoline-2-thiones and 2-halo-ketones has been developed. This metal-free approach consists in a complete chemo/regioselective formal [3 + 2] annulation that occurs in air, at 60 °C, and in water as the sole reaction medium. The opportunity to vary the substitution pattern up to six different positions, odorless manipulation of sulfurylated compounds, very easy product isolation, and mild reaction conditions are the main synthetic features of this method. The scaled-up experiment and the successive transformations of the products further demonstrate the utility of this chemistry.

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Word Cloud

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