The Research Of The Synthesis Of Ferroceneyl Deriveatives By Suzuki-miyaura Reaction And The Synthesis Of 1, 3, 4-oxadiazoline

This thesis is composed with two parts:(Ⅰ)the research of the synthesis of ferroceneyl deriveatives by Suzuki-Miyaura cross-coupling reaction;(Ⅱ)the study of the synthesis of 1,3,4-oxadiazolines(oxadiazoles).The first part:Owing to potential applications as NOL materials,liquid crystal materials, electrochemistry,biochemistry,etc,the design of new compounds incorporating the ferrocene skeleton has draw many attentions.In this thesis,we have synthesized a series of biaryl ferrocenyl chalcone derivatives by Suzuki-Miyaura cross-coupling reaction,the detailed accounts are as follow:The influence of different solvents in Suzuki coupling reaction was studied.In the reaction,the mixed solvent EA-MeOH was easy to dissolve the substrates,and also shorten the reaction times.Their structures were determined with elemental analyses,¹H-NMR spectra,¹³C-NMR spectra,IR spectra and Ms spectra.We got a single crystal of this type of compounds,and identified its structure by single crystals diffraction.These compounds crystallized in the monoclinic system with a space group P2₁/c.The plane of the thiophene ring has dihedral angles with the plane of prop-2-en-1-one and benzene ring,respectively.They are partial coplanar.We have measured these new compounds' solvatochromic effect in five kinds of solvents and found that all of the compounds in different polarity solvents have changed the displacement of maximal absorbent wavelength about 30nm,the most is 45nm.The obvious solvatochromic effect reflects indirectly that this type of chalcone analogues of ferroceneyl biaryl derivatives has great potentiality in the domain of NLO materials.The second part:Oxadiazolines and oxadiazoles have very important bioactivity such as anti-inflamemation,antibacterial,adjust plants in growing,killing pest,and other properties.So it plays important role in medicine industry and agriculture.In this thesis,2-chloronictinic hydrazine reaction with arylaldehydes(arylketone)produced corresponding hydrazones.Then these hydrazones respectively cyclodehydrated with acetic anhydride to afford 3-acetyl-2-aryl-5-(3-(2-chloropyridin))-1,3,4-oxadiazolines and 2-aryl-5-(3-(2-chloropyridin))-1,3,4-oxadiazoles.In the study,we obtained nine oxadiazolines and four oxadiazoles in the same condition.There weren't papers covered cyclization of hydrazones with acetic anhydride giving 1,3,4-oxadiazoles.So,We investigated the 4-chlorobenzylidene-2-chloronicotinic acid methylhydrazone cyclodehydrated with acetic anhydride.We obtained oxadiazoline at about 90℃,and obtained oxadiazole in refluxing.We speculate that the hydrogen atom and acetyl of some oxadiazolines is easy to leave and give oxadiazole as the reaction temperature ascending and the time prolonging.This reaction we need to investigative in detail.These compounds' structures were determined with elemental analyses,¹H-NMR spectra,¹³C-NMR spectra,IR spectra and Ms spectra. We identified two crystal structure of two type of compounds by single crystals diffraction.These compounds crystallized in the monoclinic system with a space group P2₁/n.Biology activity of these compounds are under examination.