Imide Acid And Organic Carboxylate Microwave Synthesis, Characterization, And Nature Study

As a special synthesis method, microwave technology opened a new way in chemistry synthesis field. In this dissertation, under microwave irradiation, one-step synthesis of imide by using anhydrides with amines was studied,and microwave-promoted synthesis of series of organotin carboxylates by reaction of anhydride, dicarboxylic acid and N,N-tetrafluoro (chloro)-phthaloyl-α-amino acids with organotin oxide or hydroxide was also discussed. 73 new compounds were synthesized and characterized by elemental analysis, IR, NMR spectra; and crystal structure of 17 compounds were determined. Antibacterial activities and antitumour activities of topical compounds were studied. The variations on structure and property were also discussed.First, under microwave irradiation, a series of imide compounds were synthesized By the reaction of different anhydrides and chiralα- amino acids, substituted anilines, crystal structures of N-Cl₄C₆-(CO)₂NCH (CH₂(C₆H₄C₂H₂N), COOH,N-F₄C₆(CO)₂NCH₂-COOH, N-F₄C₆(CO)₂NC₆H₄NO₂-o, N-F₄C₆(CO)₂NC₆H₄NO₂-m, N-F₄C₆(CO)₂-NC₆H₄NO₂-p, N-F₄C₆(CO)₂NC₆H₄OH-o were resolved. And the optimum conditions of the reaction under microwave irradiation was found through discussing the reaction results at different microwave power, the different reaction time, the different solvents and the different catalysts. The yield increased 10-30% and the reaction time was was decreased from 5-10 hours to 10 minites compared with conventional method.Second, microwave technology was applied to synthesis of organotin Complexes, which can greatly shorten the reaction time compared with the conventional method. Under microwave irradiation, series of new organotin carboxylates were synthesized by reaction of anhydride, dicarboxylic acid and N,N-tetrafluoro(chloro)-phthaloyl-α-amino acids with organotin oxide or hydroxide.1. 36 new orgnotin carboxylates were synthesized by N,N-tetrafluoro(chloro)-phthaloyl-a-amino acids used with organotin hydroxide or oxide, the crystal structures of 2 tricyclohexanyltincomplexes N-Cl₄C₆(CO)₂NCH[CH₂(C₆H₄C₂H₂N)]COOSnCy₃, N-F₄C₆-(CO)₂NCH[CH₂C₆H₄C₂H₂N)]COOSnCy₃ and 2 butyltin complexes {[N-F₄C₆(CO)₂NCH₂-COOSn(Bu)₂]₂O}₂, {[N-F₄C₆(CO)₂NCH[CH(CH₃)₂]COOSn-(Bu)₂]₂O}₂were determined. The result indicated that in the tricyclohexanyltin complexes carboxyl groups were monodentate ligand, while the butyltin complexes were trapezoidal dipolymer.2. 2 tricyclohexanyltin carboxylates Cy₃SnOOCCH=CHCOOH, Cy₃SnOOC-alkanolamines; and 32 of the compounds were not reported before. Furthermore, the (C₆H₄) COOH-o were synthesized by the action of cyhexatin and maleic anhydride or phthalic anhydride under microwave irradiation. And the crystal structures of them were determined. The result indicated that penta-coordinated one-dimensional chain structure was formed by coordination of carbonyl oxygen of free carboxyl group and it's adjacent tin atom. The former presented helical structure,while the latter presented zigzag structure.3.3 2-methyl-2-phenylpropyltin complexes o- {[Ph(CH₃)₂CCH₂]₃ Sn OOCC₆H₄COO Sn-[CH₂C(CH₃)₂Ph]₃},m-{[Ph(CH₃)₂CCH₂]₃Sn OOCC₆H₄COOSn[CH2C(CH₃)₂Ph]₃},p-{[Ph-(CH₃)₂CCH₂]₃SnOOCC₆H₄COOSn[CH2C(CH₃)₂-Ph]₃}were synthesized by the action of fenbutatin oxide and o(m,p)-phthalic acid under microwave irradiation. Furthermore, the crystal structures of them were determined. The result indicated that all of them were binuclear organotin complexes and carboxyl groups of them were monodentate ligand.4. 2 di-n-butyltin complexes [Cl₂FC₆H₂COO(Bu)₂Sn]₂O, [F₃C₆H₂COO(Bu)₂Sn]₂O were synthesized by the reaction of dibutyltin oxide and 2,4-dichloro-5-fluoro-benzoic acid or 2,4,5-trifluorobenzoic acid under microwave irradiation. And the crystal structures of them were determined. The result indicated that both of them were trapezoidal dipolymer.Third, inhibitory action of 6 organotin complexes to colibacillus were researched by microcalorimetry in thermokinetic analysis: the result indicate that the organotin carboxylates has good antibacterial; some of them were 7 times than penicillin. In vitro inhibitory effects of 3 of the organotin carboxylates on Bcap37, COLO205 H266, H460, A549 and H1792 cells were measured; the result indicated that this two compounds have antitumor activities and usually the in vitro activity was much higher than that of cis-platin.