The Research Of Dibenzo[B,F]Oxepine Nitrogen Analogues Synthesis Process And Its Application

Dibenzo[b,f]oxepine is a very important structure of the nucleus in medicinal chemistry, which the tricyclic structure of biological activity caused by one of the most extensive attention. These structures present in the medicinal plant, containing the mother nucleus structure of natural products have been isolated, characterization. Such as dibenzo[b,f]oxepine, many including the skeleton of the natural products have also been recently separation from Artocarpus rigida, Bauhinia saccocalyx, and Cercis chinensis root. Some of these structures exhibit excellent biological and medicinal activity, and their derivatives in industry are also widely used.In this paper, the main contents and conclusions:1.2-(2-hydroxyphenyl)acetonitrile with2-chloroquinoline-3-carbaldehyde as raw materials to synthesis of benzo[6,7]oxepino[2,3-b]quinoline, dioxane as solvent, cesium carbonate as catalytic base (3equivalent), reaction temperature120C, microwave reaction1h.2. Select a series of electron-withdrawing or electron-donating groups substituted2-(2-hydroxyphenyl)acetonitrile and2-chloroquinoline-3-carbaldehyde synthesis is a series of benzo[6,7]oxepino[2,3-b]quinoline.The first is2-(2-hydroxyphenyl)acetonitrile and2-chloroquinoline-3-carbal-dehyd as the starting material to synthesis benzo[6,7]oxepino[2,3-b]quinoline and its technological route optimization.(1)the choice of bases reaction conditions for2-(2-hydroxyphenyl)acetonitrile50mg (0.3758mmol),2-chloroquinoline-3-carba-ldehyd75mg (0.5637mmol), dioxane (solvent,3mL), microwave120℃, base were1.1274mmol potassium carbonate (yield63%),DBU (yield18%),cesium carbonate (yield80%);(2) the choice of solvent starting material again, cesium carbonate (base), microwave120℃, the solvent for dioxane (yield of80%), toluene (yield54%), THF (yield of16%), DMF (small);(3) the choice of temperature starting material again, dioxane (solvent), cesium carbonate (base), microwave reaction temperature were80℃(yield47%),100℃(yield65%),120℃(yield80%),140℃(yield67%);(4) the choice of alkali usage starting material again, dioxane (solvent), cesium carbonate (base), microwave reaction temperature for120℃, alkali usage for0.7516mmol (yield of63%),1.1274mmol (yield of80%),1.5032mmol (yield of78%). The optimal reaction conditions to draw for2-(2-hydroxyphenyl)-acetonitrile50mg (0.3758mmol),2-chloroquinoline-3-carbaldehyd75mg (0.5637 mmol),dioxane(solvent,3mL),microwave120℃, cesium carbonate367mg (1.1274mmol).The best position to synthesize a series of structural analogues of raw materials is to select a range of electron withdrawing or electron-donating group-substituted2-(2-hydroxyphenyl)acetonitrile and2-chloroquinoline-3-carbalde-hyd, mutual cross-reaction can be synthesizeda series of nitrogen-containing heterocy-clic benzo[6,7]oxepino[2,3-b]quinoline analogs. Finally, analysis shows that the experimental results of this study benzo[6,7]oxepino[2,3-b]quinoline synthesis conditions relative to the existing analogue synthesis process, its raw material is cheap and easy to get on the environmental pollution, and mild reaction conditions,easy to operate,high yield but also to fill the simple,apply a wide benzo[6,7]oxepino[2,3-b]-quinoline potential industrial production value and the blank of the method for synthesis of quinoline derivatives and to study its biological activity, as well as exploring the application of the fluorescent material.