The Synthesis Of Indoles By One-pot Heck Reaction And The Synthesis, Characterization And Icon Recognition Of Toluene-4-sulfonate Derivations

Because of the great virtue of Heck reaction and one-pot reaction, It is attractmany attention that how to synthesis indoles by the two methods. And It had gainedmany progress. But It is still a problem that how to synthesis indoles through one-potreaction with o-haloaniline and open-chain ketone. Hereon, we synthesised3-ethoxycarbonyl-2-methylindole through one-pot Heck reaction with o-bromoanilineand open-chain ketone ethyl acetoacetate. When use Pd(OAc)₂ as catalyst. We tryseveral ligands in the catalytic system: Phosphine ligands such as PPh₃,p(o-tol)₃,dppeand Non-phosphine ligands such as cabene(1) and cabene(2). We find when we usePd(OAc)₂ as catalyst. The Non-phosphine ligands cabene(1) and cabene(2) are worsethan Phosphine ligand. And Monodentate ligands PPh₃,p(o-tol)₃ are better thanBidentate ligand dppe. And we find that the solvent of DMF and alkali K₃PO₄ isbetter than other solvent and alkali in the Heck reaction.When use PdCl₂ as catalyst,CTAB as additive, we find a better catalytic system to synthsis indoles throughone-pot heck reaction with o-bromoaniline and open-chain ketone ethyl acetoacetate.We synthesis three toluene-4-sulfonate derivations and get their crystals. Theinclusion interaction of Host with Guest are tested by Fluorimetric Method. The resultof molecular recognition test of compounds (1),(2),(3) shows that all of the Hostmoleculars have strong complexation to Fe³⁺. Also compound(1) has complexationto Cu²⁺. We discuss the mechanism of recognition of the compounds. As the"key-lock" theory, we find that the room size and shape matching betweenHost-Guest plays an important and key role. We find compound(1) and compound(3)has similar cavity structure for their similar complex constant of compound(1) andcompound(3) with Fe(â…¢)(K_Fe¹=1.0764×10⁴ L/mol, K_Fe³=8.103×10³ L/mol). Bothof them form stable 1: 1 type complexes with Fe³⁺; compound(2) can form stable 1: 2type complexe with Fe³⁺. and the complex constant can reach 1.98×10⁸ L/mol, wethink compound(2) and Fe³⁺ form a stange sandwich structure.