Synthesis Of1,3-dihydro-benziso-thiazole-2,2-dioxide-3-spiro-4’-isoxazole Spiro Compounds

Benzisothiazole derivatives are widely used as agricultural chemicals andpharmaceutical agents, because of the biological activities they owned.Benzisothia-zole2,2-dioxide derivatives that have a variety of biological activityand pharmacolo-gical activity are of very important organic skeleton structures, sothey are widely used as the central nervous system sedative, central nervous systemstimulant, progesterone withdrawal resistance activator and antihypertensive drugs.Isoxazole derivatives are of great significances in drug research and development,the catalytic reaction, organic synthesis and electrochemical fields, because of itsstructure containing N, O two kinds of impurity atoms.In this paper, benzoisothiazole2,2-dioxide derivatives as synthons, a new typebenzisothiazole-2,2-dioxide-3-spiro-4’-spiro compounds was reacted with the nitrateketone dipole body. Currently, the synthetic methods for such compounds has notbeen reported. Therefore, the establishment of the method for building with similarscrew ring structure unit or skeleton of heterocyclic compound provides a newmethodology basis.In this paper, we accomplished the following works:(1) o-chloroaniline as rawmaterial, N-methyl-1,3-dihydro-benzo thiazole-2,2-oxides was produced withreactions of methane sulfonyl chloride acylation, methyl iodide methylation reaction,molecular inner ring in order. To this part, we carefully studied the cyclizationreaction and determined the optimum reaction conditions, namely sodium amide asalkali, liquid ammonia as solvent reaction under the condition of6hours, and total yield reached74%.(2) a series of1-methyl-1,3-two hydrogen benzo isothiazolin-2,2-dioxide three double bond derivatives was reacted via Knoevenagel condensa-tion by condensating1-methyl-1,3-dihydro-benzo thiazole-2,2-oxides with acetalde-hyde, chlorobenzene formaldehyde, aldehyde and two ethyl butanal ring in the baseof the catalyst. And we discussed the solvent reaction, temperature and time of theKnoevenagel condensation.(3)4groups of isomers of benzene and different thia-zole screw different oxazole spiro compounds, namely1-methyl-1,3-dihydro-benzothiazole-2,2-dioxide-3-spiro-4’-different oxazole spiro compounds were synthetisedby using1-methyl-1,3-two hydrogen benzo isothiazolin-2,2-dioxide three doublebond derivatives and alpha-phenyl-N-methyl nitrate occurred1,3-dipolar. Thesecompounds have not been reported. Compounds were characterized by1H NMR and13C NMR for determining the structure.