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...
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Veröffentlicht in: | Journal of organic chemistry 2024-04, Vol.89 (7), p.4628-4646 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.3c02903 |