Fenantrolinyum n-ilidlerin 1,3-dıpolar halka katılma tepkimelerinin incelenmesi

In this study, 1,3-dipolar cycloadditions reactions of (Z) substituted arylidene oxazolones to phenanthrolinium N-ylides were carried out for the first time. In the first stage of the work a number of substituted arylidene oxazolones as dipolarophilic structures were prepared according to the literature procedures. Some of them are novel compounds and not reported previously. Both electron-withdrawing and electron-releasing groups were selected on the starting arylidene oxazolones. In the second part, the 1,3-dipolar cycloaddition reaction of phenanthrolinium ylides prepared from phenanthroline and phenacyl bromide with (Z)-substituted arylidene oxazolones afforded novel aryl substituted spiro[oxazole-4,10?-pyrrolo[1,2-a][1,10]phenanthrolin]-5-ones, regioselectively. Totally, 15 novel aryl substituted spiro oxazolo [1,10] phenanthrolines including three chiral centers were obtained. The structures and stereochemical configurations of new aryl substituted spiro oxazolo [1,10] phenanthroline were elucidated by means of IR, NMR, 2D NMR, MASS, single crystal X-Ray Diffraction spectra and physical characteristics (melting points and Rf values).