Molecules
(Apr 2023)
A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
Nicolai A. Aksenov,
Nikolai A. Arutiunov,
Igor A. Kurenkov,
Vladimir V. Malyuga,
Dmitrii A. Aksenov,
Daria S. Momotova,
Anna M. Zatsepilina,
Elizaveta A. Chukanova,
Alexander V. Leontiev,
Alexander V. Aksenov
Affiliations
Nicolai A. Aksenov
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Nikolai A. Arutiunov
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Igor A. Kurenkov
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Vladimir V. Malyuga
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Dmitrii A. Aksenov
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Daria S. Momotova
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Anna M. Zatsepilina
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Elizaveta A. Chukanova
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Alexander V. Leontiev
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
Alexander V. Aksenov
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
DOI
https://doi.org/10.3390/molecules28093657
Journal volume & issue
Vol. 28,
no. 9
p.
3657
Abstract
Read online
A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating.
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