Baykova Svetlana O, Baykov Sergey V, Solodyankina Olga V, Boyarskiy Vadim P
Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, St. Petersburg 199034, Russia.
J Org Chem. 2024 Sep 6;89(17):12094-12103. doi: 10.1021/acs.joc.4c00974. Epub 2024 Aug 21.
We have developed a convenient protocol for synthesizing -(2-pyridyl)-substituted 4-(amino)quinazolin-2(1)-ones by reacting ,-dimethyl-'-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of ,-dimethyl-'-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)-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%.
我们已经开发出一种简便的方法，通过使α,α-二甲基-α-吡啶基脲与2-氨基苯甲腈反应来合成α-(2-吡啶基)-取代的4-(氨基)喹唑啉-2(1)-酮。该方法基于α,α-二甲基-α-吡啶基/喹啉基脲在热活化下作为掩蔽异氰酸酯的能力，随后4-亚氨基-3-(杂芳基)-3,4-二氢喹唑啉-2(1)-酮发生Dimroth重排。该反应在120°C下于N,N-二甲基甲酰胺（DMF）中或无溶剂条件下进行，此方法已制备出28种具有吡啶或喹啉取代基的4-氨基喹唑啉酮衍生物，产率高达92%。
