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以2-溴甲基-3-喹啉甲酸乙酯(1)为底物,分别与α-萘酚和β-萘酚“一锅法”高产率合成了2-(α-萘氧甲基)-3-喹啉甲酸(2a)和2-(β-萘氧甲基)-3-喹啉甲酸(2b).化合物2a,2b用Eaton试剂(五氧化二磷-甲基磺酸)作为环化试剂,发生分子内Friedel-Crafts酰基化反应得到两种新型闭环产物:萘并[2’,1’,6,7]氧杂并[3,4-b]喹啉-7(14H)-酮(3a)和萘并[1’,2’,6,7]氧杂并[3,4-b]喹啉-15(8H)-酮(3b).化合物3a,3b在氢氧化钾的乙醇-水溶液中经1,2-Wittig重排和空气氧化生成萘并[2,1-b]吖啶-7,14-二酮(4a)和萘并[1,2-b]吖啶-7,14-二酮(4b).所合成新化合物2a～4a,2b～4b的结构通过IR,UV,1HNMR,MS和元素分析进行了确认.测定了化合物2a～4a,2b～4b在三氯甲烷中的紫外光谱和化合物3a,4a和3b,4b的固体荧光光谱,2a～4a,2b～4b在三氯甲烷中的最大吸收峰分别位于280,261,312,273,256和313nm;3a,4a和3b,4b在固态状态下的最大发射波长分别为350,300,274和330nm.
The synthesis of 2- (α-naphthalene oxide) with high yield of 2-bromomethyl-3-quinolinecarboxylic acid ethyl ester (1) Methyl) -3-quinolinecarboxylic acid (2a) and 2- (β-naphthyloxymethyl) -3-quinolinecarboxylic acid (2b). Compounds 2a, 2b were prepared using Eaton’s reagent (phosphorus pentoxide- ) As a cyclization reagent, intramolecular Friedel-Crafts acylation reactions give two novel ring-closure products: naphtho [2 ’, 1’, 6,7] oxazepin [3,4- b] (3a) and naphtho [1 ’, 2’, 6,7] oxa [3,4-b] quinolin-15 (8H) 1,2,4-diketone (4a) and naphtho [1,2-b] acridine-7,14-dione (4a) were produced by 1,2-Wittig rearrangement and air oxidation of potassium hydroxide in ethanol- ] Acridine-7,14-dione (4b) The structures of the synthesized novel compounds 2a to 4a, 2b to 4b were confirmed by IR, UV, 1HNMR, MS and elemental analysis. The compounds 2a to 4a and 2b ~ 4b in chloroform and the solid state fluorescence spectra of compounds 3a, 4a and 3b, 4b, the maximum absorption peaks in 2a ~ 4a, 2b ~ 4b in chloroform are located at 280,261,312,273,256 and 313nm, respectively; 3a, 4a and 3b, 4b in the solid state of the maximum emission wavelength 350,300,274 and 330n m.