He Xinhua, Aglio Tharcilla, Deschamps Jeffrey R, Rai Rachita, Xue Fengtian
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201.
Naval Research Laboratory, Code 6930, 4555 Overlook Ave., Washington, DC 20375.
Tetrahedron Lett. 2015 Mar 11;56(11):1441-1444. doi: 10.1016/j.tetlet.2015.01.188.
We report a facile synthesis of 1,2-dihydro-2-oxo-4-quinolinyl phosphates (-) starting from 2-acyl-benzoic acids (-) in the presence of phosphoryl azides via a one-pot cascade reaction involving a Curtius rearrangement, an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate, and an addition-elimination of the enol oxygen to the phosphoryl azide. During the reaction three new bonds are formed under mild conditions to yield 1,2-dihydro-2-oxo-4-quinolinyl phosphates in modest yields.
我们报道了一种简便的合成方法，以2-酰基苯甲酸为起始原料，在叠氮化磷存在下，通过一锅串联反应合成1,2-二氢-2-氧代-4-喹啉基磷酸酯（-），该反应涉及库尔提斯重排、烯醇碳对异氰酸酯中间体的分子内亲核加成以及烯醇氧对叠氮化磷的加成消除。在反应过程中，在温和条件下形成了三个新键，以适度的产率得到1,2-二氢-2-氧代-4-喹啉基磷酸酯。
