2-芳基-3-羟基-4,9-二氢芳庚并吡喃-4,9-二酮类化合物的合成研究

Study of synthesis of 2-Aryl-3-hydroxy-4,and 9-dihydrocyclo hepta[b]-4,9-diones-

以3-乙酰基酚酮(1)为原料,与自制的苯基三甲基三溴化胺在四氢呋喃中反应2h后,加水稀释得到甲基上单溴化产物3-(2-溴代乙酰基)酚酮(2)。化合物(2)与取代苯甲醛类化合物(3a-i)在以甲醇为溶剂的条件下,于冰水浴中滴加氢氧化钠溶液,反应3h闭环,酸化后即得类黄酮型缩杂环酮的一系列化合物(4a—i),其中4b—4f是未见报道的新化合物。所有化合物的结构通过红外光谱、液相色谱分析及物理常数的测定得以证实。

3-acetyltroplone was dissolved in tetrahydrofuran and then PTM ABr3 prepared by ourselves was added into the solvent. The mixture was stirred for 2 hr,and then diluted by water to get 3-（2-bromoacetyl）troplone（2）. Compound 2 was mixed with a series of substuted denzaldehydes compounds （3a-i） in methanol. A solution of sodium hydroxide was added to the stirred mixture at icewater temperature. After acidulation, these compounds of 2-aryl- 3-hydroxy-4,9-dihydrocyclohepta[-b-] pyran-4, amd 9-diones （4a-i）were obtained. Products 4b-4f were unreported compounds. All the soruetures of these compounds were confirmed by IR,hplc and physical constants.