Reaction Behavior Study Of Dichloronitroalkene And Their Application

Nitroalkene is a hot research area in organic chemistry in recent years because of its unique chemical properties and reaction sites. As a synthon, it can participate in many organic reactions, it can react with a variety of electrophiles easily, and frequently-appeared as an intermediate or structural fragment in organic and medicinal chemistry. In this dissertation, the application of nitroalkenes as an organic synthon for access of 1,3,4-oxadiazoles, N-phenylacetamides and quinazolinones was investigated.1. The reactions of hydrazide derivatives with 1,1-dichloro-2-nitroethene were studied. This kind of 1,3,4-oxadiazoles structure is novel and the synthetic method has not been reported elsewhere. This protocol featured by high yields, purification simplicity, water-based reaction medium, energy efficiency, no addition of catalysts and high substrate applicability. The total of nineteen 1,3,4-oxadiazole derivatives were synthesized2. A green methodology was established for direct amidation of anilines using l,l-dichloro-2-nitroethene. The new protocol provides convenient N-nitroacetylation for the anilines. The amidation process was accomplished in water and the products can be easily separated by filtration. This novel procedure provides an efficient and catalyst-free method for direct amidation of aniline derivatives using 1,1-dichloro-2-nitroethene.3. The reactions of 2-aminobenzamide derivatives with 1,1-dichloro-2-nitroethene were studied. This constructed quinazolinones structure is novel and the protocol has not been reported elsewhere. This protocol featured by high yields, purification simplicity, water-based reaction medium, energy efficiency, high substrate applicability and no addition of catalysts.