Regioselective Synthesis of 1‑Sulfanyl- and 1‑Selanylindolizines

We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (11), p.7189-7198
Main Authors: Penteado, Filipe, Gomes, Caroline S, Perin, Gelson, Garcia, Cleisson S, Bortolatto, Cristiani F, Brüning, César A, Lenardão, Eder J
Format: Article
Language:English
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Summary:We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 °C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00871