Isatin-Based Domino Reaction For The Diversity-Oriented Synthesis Of Spirooxindole Derivatives

The thesis includes five parts.The first part shows the application of isatin-based domino reactions for thesynthesis of spirooxindole derivatives with highly evidently biologically activities homeand abroad, the significance and base of the selection of the subject, the original pointsand the research methods.The second part investigates a high-efficient green approach to spirooxindolesperformed by reacting cyclic-1,3-dicarbonyl substrates, isatins and malononitrile asstarting materials in water under microwave irradiation without any catalysts. Thereactions showed a broad substrates of using readily available and inexpensive startingmaterials of various isatins, malononitrile and cyclic-1,3-dicarbonyl compounds.Particularly, this green synthesis shows several attractive characteristics such as the useof water as the reaction medium, simple conditions, short reaction periods, easywork-up, straightforwardness of the procedure and reduced waste production by the lackof any requirement for catalysts.The third part develops a naphthoquinone-and diamine-based microwave-assistedreaction. The reaction of naphthoquinone, diamine, isatin and malononitrile (orcyclic-1,3-dicarbonyl substrates) in water catalyzed by HOAc underwent condensation,Michael addition and intramolecular cyclization sequence to afford a series ofspiro-substituted benzo[a]pyrano[2,3-c]phenazine-1,3’-indoline derivatives undermicrowave irradiation. The multicomponent domino approach construscts up to four orfive σ bonds including four C-N bonds and a quaternary carbon center by performingthe reaction in one-pot fashion in water under microwave irradiation in the absence ofany strong acids, metal catalysts or other promoters.The fourth part involves a facil and high-effient approach to cyclic-1,5-dicarbonylderivatives with indole and thioether nucleus by reacting two equi of α-thiocyanateketones and a equi of isatin as starting materials in EtOH catalyzed by NaOH undermicrowave irradiation. The derivatives, including both indole and thioether nuleus, aswell as two carbonyl groups, are important synthetic intermediates in organic chemistry.Besides, when isatin is replaced by2,2-dihydroxy-2H-indene-1,3-dione, the reation stillcan be performed easily. The fifth part develops a new and high-efficient domino approach to acridine fusedpyrrole derivatives with highly potentially biological activities performed by reactingdiamitone and isatin as starting materials in HOAc under microwave irradiation. Thederivatives including indole nuleus was formated via a series of complicated changes bythe open-loop of the isatin. The reaction process is a representative domino reation,which was performed via a series of complex changes with very short times, but gainingexciting results.All the structures of the products were determined by1H NMR, IR and HRMS.Furthermore, the structures of some products were confirmed by X-ray analysis. Themicrowave-assisted reactions mentioned above have advantages of simple conditions,short reaction periods, easy work-up, straightforwardness of the procedure.