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4-喹诺酮-2-羧酸甲酯衍生物的制备,一般是用苯胺衍生物与丁炔二酸二甲酯反应,生成α-(取代苯胺基)丁烯二酸二甲酯(1),继之在二苯醚中约260℃加热环合而获得。我们用间氨基苯酚与丁炔二酸二甲酯在甲醇中反应,所得黄色固体经鉴定为7-羟基-4-喹诺酮-2-羧酸甲酯(2);除去固体后的滤液在甲醇-盐酸中回流还能生成2。若用间苯二胺与丁炔二酸二甲酯反应,则生成7-氨基-4-喹诺酮-2-羧酸甲酯(3)(产率20%)和N,N′-二(1,2-双-甲氧羰基乙烯基)间苯二胺(4)(产率4.8%)。这样就不需要再在二苯醚中进行环合。2与3的易于制备,显示氨基和羟基的活化作用。2和3在室温分别与醋酐-吡啶反应,可得乙酰化物5和6.2和3在二甲基甲酰胺中与乙氧草酰氯(ethyloxalyl chloride)反应,可分别生成化合物7和8。
The preparation of 4-quinolone-2-carboxylic acid methyl ester derivatives is generally carried out by reacting the aniline derivative with dimethyl butynedioate to form dimethyl α- (substituted anilino) butenoate (1), Followed by heating at about 260 ° C in diphenyl ether for cyclization. We reacted with m-aminophenol and dimethyl butynidic acid in methanol, and the resulting yellow solid was identified as methyl 7-hydroxy-4-quinolone-2-carboxylate (2) Hydrochloric acid reflux can generate 2. If m-phenylenediamine is reacted with dimethyl butynedioate, methyl 7-amino-4-quinolone-2-carboxylate (3) is produced in 20% yield and N, , 2-bis-methoxycarbonylvinyl) m-phenylenediamine (4) (yield 4.8%). This eliminates the need for cyclization in diphenyl ether. Ease of preparation of 2 and 3, showing the activation of amino and hydroxyl groups. Reaction of 2 and 3 with acetic anhydride-pyridine, respectively, at room temperature provided that acetylates 5 and 6.2 and 3 were reacted with ethyloxalyl chloride in dimethylformamide to yield compounds 7 and 8, respectively.