Access to 4‑((Pyridin-2-yl)amino)quinazolinones via Annulation of 2‑Aminobenzonitriles with N′‑(Pyridin-2-yl)‑N,N‑dimethyl Ureas
We have developed a convenient protocol for synthesizing N-(2-pyridyl)-substituted 4-(amino)quinazolin-2(1H)-ones by reacting N,N-dimethyl-N′-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of N,N-dimethyl-N′-pyridyl/quinolinyl ureas to act as masked isocyanates under ther...
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Veröffentlicht in: | Journal of organic chemistry 2024-09, Vol.89 (17), p.12094-12103 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | We have developed a convenient protocol for synthesizing N-(2-pyridyl)-substituted 4-(amino)quinazolin-2(1H)-ones by reacting N,N-dimethyl-N′-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of N,N-dimethyl-N′-pyridyl/quinolinyl ureas to act as masked isocyanates under thermal activation, followed by a Dimroth rearrangement of 4-imino-3-(hetaryl)-3,4-dihydroquinazolin-2(1H)-ones. Conducted at 120 °C, either in DMF or under solvent-free conditions, this approach has produced 28 derivatives of 4-aminoquinazolinones, featuring pyridine or quinoline substituents, with yields of up to 92%. |
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ISSN: | 0022-3263 1520-6904 1520-6904 |
DOI: | 10.1021/acs.joc.4c00974 |