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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.

Authors :
Baykova SO
Baykov SV
Solodyankina OV
Boyarskiy VP
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