Tandem Reactions Based On 3-oxo-N-arylbutanamides

One of the hot topics in the research of organic synthetic chemistry is to construct complex compounds from simple and readily available starting materials. C-C bond and C-N bond formation reactions are quite important in organic chemistry. Tandem reactions have distinct advantages of high efficiency and minimized waste, which meet the requirement of green chemistry, as the developmen tendency in morden organic chemistry.Disubstituted 3-oxo-N-arylbutanamide compounds have many reactive sites, thus providing us an opportunity to perform various types reactions.In this paper, I focused on the tandem reactions of 3-oxo-N-arylbutanamide compounds with o-phthalaldehyde and three-component reaction of 3-oxo-N-arylbutanamide compounds and malononitrile and aliphatic amines. The main research is as follows:1. A novel domino reaction based on o-phthalaldehyde and 3-oxo-N-arylbutanamide 1 has been developed which allows one-pot and efficient synthesis of structurally complex spiroindan-2,2'-pyrrolidines 2 and 3 with complete regioselectivity and high stereoselectivity from acyclic precursors. The reaction scope was explored and the possible mechanism was presented.2. An efficient synthesis of fully substituted pyridin-2(1H)-ones was developed via three-component one-pot reactions of readily available 1-acetyl-1-carbamoyl cyclopropanes, malononitrile and cyclic secondary amines. It was observed that the ring-opening of the cyclopropane ring favors the formation of the pyridin-2(1H)-ones.