A practical and mild chlorination of fused heterocyclic N-oxides |
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| Institution: | 1. Longwood Biopharmaceuticals Co. Ltd, Tianjin International Joint Academy of Biomedicine, Tianjin 300457, China;2. School of Medicine, Nankai University, Tianjin 300071, China;1. Departments of Medicinal Chemistry, Merck & Co., Inc., West Point, PA 19486, USA;2. Neuroscience Biology Discovery, Merck & Co., Inc., West Point, PA 19486, USA;3. Pharmacology, Merck & Co., Inc., West Point, PA 19486, USA;1. Department of Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, China;2. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China;3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;4. School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China;1. Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH 43210, USA;2. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA |
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| Abstract: | Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated. |
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| Keywords: | Chlorination Vilsmeier reagent Quinoline Isoquinoline |
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