USE OF ARYL METHYLKETONE IN THE SYNTHESIS OF SOME HETEROCYCLIC COMPOUNDS AS EXPECTED FOR ESTIMATING HEAVY METALS

Abstract

The thesis deals with the synthesis of some different heterocyclic compounds containing benzocoumarin moiety using 3-(2'-formyl-1'-chlorovinyl)-5,6-benzocoumarin as a key starting material which was synthesized from the reaction of 3-acetyl-5,6-benzocoumarin with DMF POCh . Study of the chemical reactions of some synthesized heterocyclic compounds towards nitrogen nucleophile reagents and carbon electrophile reagents to produce different new benzocoumarin compounds, expected for used in estimation heavy metals. It is classified into three parts. I-1-Synthesis and some reactions of3-[(l'-substituted) pyrazol-5'-yl]-5,6 benzocoumarin (3). As a point of interest the author tried to synthesise 3-[(1'-substituted) pyrazol-5'-yl]-5,6 benzocoumarins (3a) , and study the chemical behavior of pyrazole ring in compound (3,) towards different carbon electrophile reagents ,such as alkylation and/or olefinic compounds under Michael reaction conditions and/or acid chlorides (Scheme 1) . Alkylation of (3,) with alkyl halide (namely, benzyl bromide, phencyl bromide, ethylchloroacetate and dimethyl sulphate) afforded the corresponding 3-[(1'-alkyl)pyrazol-5 yl]-5,6-benzocoumarins (4a) and (12) respectively. Condensation of (4,·) with aromatic aldehydes and (4) with hydrazine hydrate gave the corresponding 3-[(1'-(2"-ary!-1-alkylviny))pyrazol-5'-y1]-5,6-benzocoumarins (5,) and 3 [(l'-hydrazinocarbonyMmethyl)pyrazol-5'-yl]-5,6-benzocoumarin (6) respectively. Compound (3,) reacted with olefinic compounds (such as acrylonitrile and methyl acrylate) gave the corresponding 3-[(1'-alkyl) pyrazol -5'-yl]-5,6-benzocoumarins (7,). Treatment of compound (7) with sodium azide and (7) with hydrazine hydrate afforded the corresponding 3-[1'-(tetrazol-5"-ylethy!) pyrazol-5'-yl]-5,6-benzocoumarin (8) and 3-[1 (hydrazinocarbonyl ethyl)pyrazol -51-yl]-5,6-benzocoumarin (9) respectively. Acylation and/or benzoylation of (3,) with acid chlorides (namely, acetyl chloride, chloroacetyl chloride and benzoyl chloride) gave the corresponding 3-[1'- (alkyl -carbonyl) pyrazol -5'-yl]-5,6-benzocoumarins (10 ~). Compound (10%) reacted with primary aromatic amines afforded the corresponding 3-[1 (arylaminoacetyl) pyrazol-5'-yl]-5,6-benzocoumarins (11~,) The structure of the new prepared compounds were confirmed chemically and spectroscopically.