Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N′-(Pyridin-2-yl)-N,N-dimethyl Ureas,The Journal of Organic Chemistry

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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
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-08-21 , DOI: 10.1021/acs.joc.4c00974
Svetlana O Baykova ₁ , Sergey V Baykov ₁ , Olga V Solodyankina ₁ , Vadim P Boyarskiy ₁

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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%.

中文翻译：

通过 2-氨基苯甲腈与 N'-(吡啶-2-基)-N,N-二甲基脲成环获得 4-((吡啶-2-基)氨基)喹唑啉酮

我们开发了一种通过N , N-二甲基-N'-吡啶脲与 2-氨基苯甲腈反应合成N- (2-吡啶基)-取代的 4-(氨基)喹唑啉-2(1 H )-酮的简便方案。该方法依赖于N , N-二甲基-N'-吡啶基/喹啉基脲在热活化下充当掩蔽异氰酸酯的能力，然后进行 4-亚氨基-3-(杂芳基)-3,4-二氢喹唑啉的 Dimroth 重排-2(1 H )-1。该方法在 120 °C、DMF 或无溶剂条件下进行，生成了 28 种带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%。

更新日期：2024-08-21

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