Multicomponent Reactions Of Azaaromatic Quaternary Ammonium Salts And 1,3-indandione

The azaaroamtic quaternary ammonium salts can be formed by the alkylation of azaaromatic compounds with reactive alkylating reagents, which can be deprotonated to form the reactive nitrogen ylides in the presence of base. These nitrogen ylides have versatile reactivities and can undergo various reactions such as Michael addition, nucleophilic addition, nucleophilic substitution,1,3-dipolar cycloaddition and rearrangement reactions. They are always used as important synthons to construct multisubstituted heterocyclic compounds in synthetic organic chemistry. The obtained nitrogen-containing heterocyclic compounds are the basic skeletons of many natural drugs and bioactive molecules. On ther other hand,1,3-indandiones havc β-dicarbonyle structure and are very reactive compounds, 1,3-Indandione can form dipolar unsaturated compounds with active carbonyl compounds, which have been used for synthesis of various types of compounds for different purposes. Thus, they play a decisive role in the drug synthsis. In this thesis, we carried out the synthsis of versatile heterocyclic compounds by one-pot multicomonent reactions of quaternary ammonium salts and 1,3-indandione with other substrates.1. An efficient synthetic procedure for the functionalized spiro[indan-2,1’-pyrrolo[2,1-a]isoquinolines] derivatives were successfully developed by domino reactions of N-phenacylisoquinolinium bromide with isatin derivatives and 1,3-indandione in the presence of triethylamine in ethanol at room temperature. Totally, nineteen spiro[indan-2,1’-pyrrolo[2,1-a]isoquinoline] derivatives were prepared and characterized by IR,1H NMR,13C NMR, HRMS spectroscopy. The single crystal structure of one product was determined by X-ray diffraction method.2. Under the catalysis of triethylamine, the reaction of N-phenacylpyridinium bromides or N-ethoxycarbonylmethylenepyridinium bromide with istain and 1,3-indandione in refluxing ethnaol generated a series of novel seven-member heterocycles with expansion of isatinyl ring. The similar 4-dimethylamino pyridium salts can also be used in this reaction. All the products were characterized by IR,1H NMR,13C NMR,HRMS spectroscopy. The single crystal structures of two products were determined by X-ray diffraction method.3. A series of functionalized spiro compounds were efficiently synthesized by the reaction of N-phenacylquinolinium bromide,1,3-indandione and aromatic aldehydes with triethylamine as base under the room temperature. All the products were characterized by IR, ’H NMR,13C NMR, HRMS spectroscopy. The single crystal structure of one product was determined by X-ray diffraction method.