Regioselective Synthesis of Substituted 4-Alkylamino and 4-Arylaminophthalazin-1(2H)-ones

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• 作者：Subramaniam Krishnananthan ; Daniel Smith ; Dauh-Rurng Wu ; Shiuhang Yip ; Prashantha Gunaga ; Arvind Mathur ; Jianqing Li
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：81
• 期：4
• 页码：1520-1526
• 全文大小：350K
• ISSN：1520-6904

文摘

An efficient regioselective synthesis of substituted 4-alkylamino and 4-arylaminophthalazin-1(1H)-ones 5 is described. This new method features the formation of substituted phthalazin-1(1H)-ones 3 by the reaction of 2-formylbenzoic acids 1 or 3-hydroxyisobenzofuran-1(3H)-ones 2 with hydrazine to generate phthalazin-1(2H)-ones 3. Subsequent regioselective bromination of phthalazin-1(2H)-ones 3 with benzyltrimethylammonium tribromide (BTMA-Br₃) followed by mixed copper–copper oxide-catalyzed amination of 4-bromophthalazin-1(2H)-ones 4 with primary amines generates aminophthalazin-1(2H)-ones in good overall yields.