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Abstract 2_1~-(3,4-D1chlorObenzoyl)vinYll-5(4)-oxazOlone (II)was prepared. (II) Reacted with toluene at room ~empGrature in the presence of anhydrous AlCl~ and gave the acrylamlde derivative (III), while on carrying the reaction on boiling water bath, the propionamide derivative (IV) was obtained as the main product along with minor amount of compound (III).Similarly, ring opening alkylation of (II) With £~xylene at room temperature gave the acrylamido dGrivatives (v~ and Vb).However, when the reaction was carried out on boiling water bath in the presence of anhydrous AlGI, (6 mole). The produots were (VI) as the main product together with minor amount from (v.!!).-Xylene reacted with oxazolone (II) of AlGI, (; mole) at roam temperature or on boiling water bath and gave one and the same product (VII) which can be hydrolysed to the propioniO acid derivative (VIII).The acrylami~e derivative (IX) was obtained as the main product along with minor prOduct of compound (X) by the action of ~-xylene on oxazolone (II) at room temperature. While compound (X) was obtained as a sole product when the raaction was carried out on boiling water bath. Treatment of 4_benzYlidene-2-(4’-chlorOphenyl)-5(4)- oxazolone XI with £-xylene or £-xylene in the presence of - ii - AIel, (; mole) on boiling water bath afforded hetero-ring opening followed by dearylation and gave N-aroylmethyl-~- chlorobenzamide (XII~ and b). 4_Arylidene-2-aryl-5(4)-oxazolones (XI~-!) were prepared. Aminolysis of (XI~,~,f and ~) with primary amines in ethanol gave a_arylcarbOxamido-~-arylacrylamides (XIVe-~). Also secondary amines namely, piperidine and/or morpholine reacted with (XI~,~ and i) and yielded ”_(~_cblorobenzamido)- ~-arylacrylic acid piperidide or morpholide (XVa-~). Reaction of (XI~ and 1) with ~-toluidine in acetic acid yielded the 4-arylidene imicazolinones (XVI~ end ~). Hydrazinolysis of (n~,~,~ and 1) with hydrezine in ethanol gave ~-arylamidO cinnamic acid hycrazides XVlla--drespectively. Similarly (XI~,~,f and h) condensed with phenylhydrazine in ethanol and yielded the phenylhydrazides (XVII~-~). The phenylhydrazides (XVII~ and f) were cyclised to give the triazines (XVIII~ and ~). The oX8zo1ones (XI~,£,~ and h) reacted with hydroxylamine hydrochloride in pyridine and gave 4-arylidene I-hydroxy-2_aryl-5-imidazolones (XIXa-~) which are converteo to the trlazines (XVIII~ Bnd ~)- iii -Azidolyeis o~ (II~,~,an!d~) gave the a-Itetrazolyl-(1)-1-5-arylacrylic acids (XX~-~). 4_13_NitroPhthalidGnel-2-(~-chlOrOPhenYl)-5(4)-oxazOlone (XXI) was prepared to Bee tho relative reactivity o~ lactone ring with the azlactone ring.Hydrazinolysis of (XXI), with hydrazine hy~ate gave a ~ixture of 1,4_(3_nitrophthalazindione) (XXII), and ~_chlorObenZoylglycine hydrazide (XXIII). However, hydrazinolysis of (XXI) with phenylhydrazine in athanol yielded a mixture of 3-nitro phthalic acid - diphenylhynrazida (XXIV) and ~_ChlorObenzylglyC1ne-N-phenylhydrazide (XXV).Compound (XXI) reacted with cyclohexylamine yielding the imidazolone derivatives (XXVI and XXVII) in which the steric and polar factors of both addendum and substrata had been studied.The structure assigned to the products was established from I.R. spectra (cf. Figs. 1-18) and NMR spectra (cf. Figs-19-2’). |