水介质中2-氨基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃-3-羧酸酯的有效合成.pdfVIP

2005 年第 25 卷 有 机 化 学 Vol. 25, 2005 第 12 期, 1570～1574 Chinese Journal of Organic Chemistry No. 12, 1570～1574 ·研究论文· 水介质中 2-氨基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8- 四氢苯并[b]吡喃-3-羧酸酯的有效合成 史达清*,a,b 张 姝 a 庄启亚 a,b (a 徐州师范大学化学系 徐州 221116) (b 江苏省药用植物生物技术重点实验室 徐州 221116) 摘要 水介质中在三乙基苄基氯化铵(TEBA)存在下, 芳亚甲基氰乙酸酯与 5,5-二甲基-1,3-环己二酮反应为 2-氨基-4-芳 基-7,7-二甲基-5-氧代-4H-5,6,7,8- 四氢苯并[b]吡喃-3-羧酸酯提供了一种快速、方便、高效和洁净的合成方法. 产物的结 构通过红外光谱、核磁共振氢谱、元素分析和单晶 X 射线衍射确定. 关键词 苯并[b]吡喃-3-羧酸酯, 水介质, 绿色合成 Efficient Synthesis of 2-Amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8- tetrahydrobenzo[b]pyran-3-carboxylate in Aqueous Media SHI, Da-Qing*,a,b ZHANG, Shua ZHUANG, Qi-Yaa,b a ( Department of Chemistry, Xuzhou Normal University, Xuzhou 221116) (b Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province, Xuzhou 221116) Abstract In aqueous media the reaction of arylmethylene cyanoacetate with 5,5-dimethyl-1,3-cyclohex- andione in the presence of triethylbenzylammonium chloride (TEBA) provides a fast, efficient, high-yielding and clean access to 2-amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran- 1 3-carboxylate. The structures of all compounds obtained were characterized by IR, H NMR spectra, elemental analysis and single crystal X-ray diffractometry. Keywords benzo[b]pyran-3-carboxylate; aqueous media; green synthesis 苯并吡喃类化合物是一类具有广泛的生物活