الفهرس 
COVEROnly 14 pages are availabe for public view
 |  | from | 107 |  |  |
| | | from | 107 | | |
Abstract
This study involves the synthesis of new 3(2H)-Furanones 1-acetyl-5-alkyl-3-(2-oxo-5-(4-alkylphenyl)furan-2(3H)-ylidene)indolin-2-ones (IIIa-f) &3-(5-(4-alkylphenyl)-2-oxo -furan-2(3H)-ylidene)-5-alkylindolin-2-ones (IVa-f), via the reaction of isatin derivatives (Ia-c) and β-aroylpropionic acids (IIa-b) under
traditional thermal Perkin reaction conditions and by microwave irradiation for 3 minutes at 200 ͦC (Scheme1).The reactivity of the new 2(3H)-furanone derivatives towards some nucleophilic reagents was studied.(Scheme1)The reaction of isatin derivatives (Ia-c) with β-aroylpropionic acids (IIa-b) under microwave irradiation yielded 2(3H)furanones (IVa-f) with NH group instead of
the N-acetyl group obtained from the traditional thermal Perkin reaction condition. Reaction of 3-(5-(4-alkylphenyl)-2-oxofuran-2(3H)-ylidene)-5-alkyl indolin-2-ones (IVa-d,f) in ethanol with hydrazine hydrate by stirring at room temperature involved ring opening of lactone gave the corresponding hydrazide derivatives 2-(5-alkyl-2-oxoindolin-3-ylidene)-4-oxo-4-(4-alkylphenyl)butane hydrazides (Va-e)(Scheme2).• 2-(5-alkyl-2-oxoindolin-3-ylidene)-4-oxo-4-(4-alkyl phenyl) butane hydrazides (Va,b,d,e) can be cyclized via microwave irradiation for 3 minutes at150 ͦ C in ethanol as a solvent to give the corresponding six membered heterocyclic pyridazine derivatives 5-alkyl-3-(3-oxo-6-(4-alkylphenyl)-2,3-dihydro pyridazin-4(5H)-ylidene)indolin-2-ones (VIa-d) (Scheme3).
• 5-Methyl-3-(3-oxo-6-p-tolyl-2,3-dihydro pyridazin-4(5H)-ylidene) indolin-2-one were prepared via a reaction of furanone (IVa)(0.01mol)and hydrazine hydrate(0.01mol) in ethanol(10ml) by microwave irradiation for 3minutes at 150°C, which confirmed its structure by m.p, mixed m.p experiments.
• Rreaction of 1-acetyl-5-alkyl-3-(2-oxo-5-(4-alkylphenyl) furan-2(3H)-ylidene)indolin-2-ones(IIIa-f),and3-(5-(4-methoxyphenyl)-2-oxo-furan-2(3H)-ylidene)-5-nitroindolin-2-one (IVe) with benzylamine in ethanol both by stirring at room temperature or by reflux and or by microwave irradiation for 3 minutes at room temperature, under all the mentioned conditions all gave the same product named by 2-(1-acetyl-5-alkyl-2-oxoindolin-3-ylidene)-N-benzyl-4-oxo-4-(4-alkylphenyl)butanamides (VIIa-f),N-benzyl-4-(4-methoxyphenyl)-2-(5-nitro-2-oxo-indolin-3-ylidene)-4-oxo-butanamide (VIIg) (Scheme4).
• 2-(1-alkyl-5-methyl-2-oxoindolin-3-ylidene)-N-benzyl-4-oxo-4(4-alkyl- phenyl)butanamides (VIIb,c), N-benzyl-4-(4-methoxyphenyl)-2-(5-nitro-2-oxoindolin-3-ylidene)-4-oxo-butanamide (VIIg),can be cyclized in a mix of equal molar ratio of acetic acid and hydrochloric acid by refluxing for 3 hours and or by microwave irradiation for 3 minutes at120 ͦ C to yield the corresponding pyrrolone 1-acetyl-3-(1-benzyl-2-oxo-5-p-tolyl-1,2-di -hydropyrrol-3-ylidene)-5-alkylindolin-2-ones (VIIIa-b),3-(1-benzyl-5-(4-methoxyphenyl)-2-oxo-1,2-dihydropyrrol-3-ylidine)-5-nitroindolin-2-one ( VIIIc)(Scheme5).
• The cyclized structure(VIIIb) can be obtained in one step by microwave irradiation for 3 minutes at120 ͦ C by reaction of 1-acetyl-5-chloro-3-(2-oxo-5-p-tolylfuran-2(3H)-ylidine)indolin-2-one (IIIc)with benzylamine in a mix of equal molar ratio of acetic acid and hydrochloric acid ,which confirmed its structure by m.p and mixed m.p experemints.(Scheme6)
• Reaction of 1-acetyl-3-(5-(4-methoxyphenyl)-2-oxofuran-2(3H)-ylidene) -5-methylindolin-2-one (IIId), 3-(5-(4-alkylphenyl)-2-oxofuran-2(3H)-ylidene)-5-alkylindolin-2-ones (IVa,b,d,e) and ammonium acetate in the presence of acetic acid by thermal condition and by microwave irradiation for 3minutes at150 ͦ C gave1-alkyl- 3-(5-(alkylphenyl-2-oxo-1,2-dihydro- pyrrol-3-ylidene)-5-alkylindolin-2-ones (IXa-e) (Scheme7).• 5-Methyl-3-(2-oxo-5-p-tolyl-1,2-dihydropyrrol-3-ylidene)indolin-2-one (IXb) can be obtained by microwave irradiation for 3 minutes at150 ͦ C by reaction of 5-methylisatin (Ia) with β-toloylpropionic acid (IIa) in ammonium acetate and acetic acid, which confirmed its structure by m.p and mixed m.p experiment. (Scheme8).• Treatment of pyrrolone derivatives (IXb-e) with phosphorous pentasulfide were refluxed in xylene afforded the corresponding 5-alkyl-3-(2-thioxo-5-(4-alkyl- phenyl) -1,2-dihydropyrrol-3-ylidine)indolin-2-ones (Xa-d) (Scheme9).• Alkylation of 5-alkyl-3-(2-oxo-5-(4-alkylphenyl)-1,2-dihydro- pyrrol-3-ylidine)indolin-2-ones (IXb-e) with ethylchloroacetete in dry acetone and anhydrous potassium carbonate under microwave irradiation for 3 minutes at70 ͦ C afforded the ethyl-2-(3-(5-alkyl -2-oxoindolin-3-ylidene) -5-(4-alkylphenyl)-3H-pyrrol-2-yloxy)acetates (XIa-d)(Scheme10).
• A series of sulfonamide derivatives has been synthesized by reaction of 3-(5-(4-alkylphenyl)-2-oxofuran-2(3H)-ylidene)-5-alkylindolin-2-ones (IVb,c,f) with sulfanilamide (XII) in presence of acetic acid under microwave irradiation for 3 minutes at 120 ͦC gave the corresponding sulfonamide derivatives 4-(3-(5-alkyl-2-oxoindolin-3-ylidene)-5-(alkyl phenyl)-2-oxo-2,3-dihydropyrrol-1-yl)benzenesulfonamides (XIIIa-c) (Scheme11).• Reaction of 3-(5-(4-alkylphenyl)-2-oxofuran-2(3H)-ylidene)-5-alkyl indolin-2-ones (IVb,c,f) with sulfaguanidine (XIV) in presence of acetic acid under microwave irradiation for 3 minutes at 120 ͦC gave the corresponding sulfonamide derivatives1-(4-(3-(5-alkyl-2-oxo- indolin-3-ylidene)-5-(4-alkylphenyl)-2-oxo-2,3-dihydropyrrol-1-yl) phenylsulfonyl) guanidines (XVa-c) (Scheme12).• Finally,the reaction of 3-(5-(4-alkylphenyl)-2-oxofuran-2(3H)-ylidene)-5-alkylindolin-2-ones (IVa-c,e,f) with 4-(2-aminoethyl)benzenesulfonamide (XVI) in presence of acetic acid under microwave irradiation for 3 minutes and at 120 ͦ C gave the corresponding sulfonamide derivatives 4-(2-(3-(5-alkyl-2-oxoindolin-3-ylidene)-2-oxo-5-(4-alkylphenyl)-2,3-di- hydropyrrol-1-yl)ethyl)benzene sulfonamides (XVIIa-e) (Scheme13).• The antimicrobial activity of some selected new prepared compounds were tested in vitro against different types of bacteria gram-negative [E. coli (ATCC-25922) and Shigella flexeniri dysenterie], gram-positive [Staphylococcus aureus (ATCC-25923) and Bacillus cereus], in addition to fungi [Aspergillus flavus and Candida albicans (ATCC 10231)]. Also the MIC data from these activities was also evaluated.