Microwave-Assisted One-Pot Telescoped Synthesis of 2‑Amino-1,3-thiazoles, Selenazoles, Imidazo[1,2‑a]pyridines, and Other Heterocycles from Alcohols

Primary and secondary alcohols have been converted into 2-amino-1,3-thiazoles under microwave irradiation, employing trichloroisocyanuric acid (TCCA) as a dual oxidant and chlorine source, TEMPO as a co-oxidant, and thiourea. Secondary alcohols underwent a single-stage, one-pot conversion process, w...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-04, Vol.89 (7), p.4628-4646
Hauptverfasser: Macías-Benítez, Pablo, Sierra-Padilla, Alfonso, Guerra, Francisco M., Moreno-Dorado, F. Javier
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Primary and secondary alcohols have been converted into 2-amino-1,3-thiazoles under microwave irradiation, employing trichloroisocyanuric acid (TCCA) as a dual oxidant and chlorine source, TEMPO as a co-oxidant, and thiourea. Secondary alcohols underwent a single-stage, one-pot conversion process, while primary alcohols required a two-stage, one-pot procedure. Both transformations were completed within minutes (25–45 min). The versatility of this protocol extends to the synthesis of other heterocycles, including 1,3-selenazoles, 2-aminoimidazoles, imidazo­[1,2-a]­pyridines, quinoxalines, and hydrazino thiazoles by replacing thiourea with the appropriate surrogates.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02903