Studies On The Synthesis Of Spiro-Compounds By Azomethine Ylides

The spiro compounds containing indole moiety which have significant physiological and biological activity are widely existed a variety of natural products. The 1,3-dipolar cycloaddition reaction of azomethine ylides has became an important and effective route to construction of five-membered heterocyclic ring system. In this thesis, we describe our research in detail on the preparation of spiro heterocyclic compounds by multi-component 1,3-dipolar cycloaddition reaction, and explore the reaction effect under the traditional heating and ultrasonic radiation. Four parts are included in this paper:Part one: In this part a series of novel dispiro compounds has been synthesized in high regio-selectivity and stereo-selectivity by one-pot multi-component reaction. Firstly, the pseudo-four-component reaction was investigated to synthesis of dispiro products containing two moieties of indole by the insatin, sarcosine and malononitrile with the ratio of 2:1:1 with one step. Secondly, the three components of isatin, sarcosine and dipolarophiles condensed by isatin and malononitrile were involved in forming dispiro compounds including two of different indole moieties.Part two: In this part we have studied the reaction that was taken placed under the conventional heating by three components, and the corresponding novel spiro compounds with pyrone moiety were produced in high regio-selectivity. In this reaction, the chalcones with pyrone moiety were taken as dipolarophiles, isatin derivatives and sarcosine/thioproline were treated as the source of azomethine ylides,Part three: Azomethine ylides involved in cycloaddition reactions promoted by ultrasonic radiation was studied in this part. A series of spiro compounds of pyrrole derivatives were synthesized by three components of isatin, sarcosine and chalcones with thiazole moiety under ultrasound radiation. Comparing to the traditional heating method, ultrasound chemistry takes the advantege of time saved, high yield and simple procedure.Part four: A series of novel dispiro compounds of thiazole derivatives were synthesized in high regio-selectivity by three components of isatin/ acenaphthoquinone, thioproline and chalcones with thiazole moiety under ultrasound radiation.