The Efficient Synthesis Of Oxindole And Its Derivatives

In the first chapter, we have reviewed the recent studies on the improvement of the "ways to raise atom economy and efficient synthesis methods are also summarized. The concept "waste as catalyst or promoting agents" developed recently is also introduced and reviewed. This strategy can be utilized to overcome some problems which result from the atom-uneconomical reacions, thus providing a new strategy to improve the atom econnomy in chemical process and green chemistry. Under the guidance of this strategy, we have developed a facile and efficient synthesis of oxindoles via an one-pot reaction. In this reaction, using simple and commercial available materials, a sequential SNAr/Krapcho decarboxylation/reductive cyclization reaction was realized for the formation of oxindoles, an important class of medical intermediates or building blocks of natural products.In the second chapter, we have developed a facile and efficient synthesis of C3-substitued oxindoles via a one pot Knoevenagel condensation/reduction of oxindole with carbonyl compund, using phenylmethanamine as catalyst, acetic acid as co-catalyst, NaBH4as reductive agent.With methods developed in this paper, we finished the synthesis of Semaxanib (SU5416) in92%yield,(Z/E)-3-(3-methylbut-2-en-1-ylidene)-1,3-dihydro-2H-indol-2-one in97%yield, with a single step. And we also finished the total synthesis of Soulieotine, which was previously synthesised over four steps with only23%yield, within2steps in61%yield.