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Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N '-(Pyridin-2-yl)- N , N -dimethyl Ureas.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2024 Sep 06; Vol. 89 (17), pp. 12094-12103. Date of Electronic Publication: 2024 Aug 21. - Publication Year :
- 2024
-
Abstract
- We have developed a convenient protocol for synthesizing N -(2-pyridyl)-substituted 4-(amino)quinazolin-2(1 H )-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(1 H )-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%.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 89
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39166766
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00974