2-Hydroxylation Of 1,3-Diketones And 1,4-Aza-Michael Addition Of Benzotriazole And Dienones

2-Hydroxy-1,3-dicarbonyl compounds are widely used as synthetic intermediates and common structural motif in many natural products and pharmaceuticals. The most convenient synthetic route to 2-hydroxy-1,3-dicarbonyl compounds is the direct oxidation of the corresponding 1,3-dicarbonyl compounds. In recent years, researchers have used a variety of oxidants. However, the instability and high cost are the problems of these oxidants. From an economic and ecological point of view, the air oxidation of dicarbonyl compounds is the best approach. Therefore, the exploration of the reaction using air as an oxidant without heavy metals and enlargement of the scope of substrates is becoming a daunting task.The significance of N-heterocyclic scaffolds has been recognized by their high abundance in nature, the catalytic aza-Michael addition is an important reaction within synthetic organic chemistry, as well as broad synthetic applications in pharmaceutical chemistry, biology, and material sciences, In traditional, aza-Michael addition reaction generally uses a variety of Br(?)nsted, Lewis acids and some transition metal complexes as catalysts. Considering the substantial cost and high toxicity associated with these catalysts, chemists are dedicated to finding new category of nitrogen nucleophiles, suitable acceptors and efficient catalytic system. In addition, it is worth noting that the regioselectivity for aza-Michael additions of some unsaturated ketones has many problems, It also requires to explore and find out a kind of reaction conditions with high regioselectivity.Based on surveying of literatures, the 2-hydroxylation of 1,3-dicarbonyl compounds reaction, aza-Michael reactions of benzotriazole and dienones were systematically studied. And some positive results have been achieved.The paper is divided into three chapters.Chapter ?:The progresses of synthesis and applications of 2-hydroxy-1,3-dicarbonyl compounds and the aza-Michael reactions were reviewed.Chapter ?:A novel method for the 2-hydroxylation of 1,3-diketones, using atmospheric oxygen as an oxidant, potassium fluoride as a catalyst and sodium hydroxide as a base was described. The advantages of this method are the use of green oxygen source, mild condition and high yield.Chapter ?:A selective 1,4-aza-Michael reaction of benzotriazole to dienones with KOAc as catalyst to synthesize a series of N-heterocyclic compounds was described. This protocol has advantages of mild condition, high yield and good selectivity.