The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethox... more The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethoxymethylene-1,5-diphenylpyrrolidine-2,4-dione (2). Reaction of the latter with hydrazine hydrate, secondary amines 7a-c or urea afforded the corresponding 3-substituted aminomethylene-1,5-diphenylpyrrolidene-2,4-diones 3, 8a-c or 9. On the other hand, condensation of 3 with veratraldehyde (5a) yielded 3-[(3,4-dimethoxybenzylidene)hydrazinomethylene]-1,5-diphenylpyrrolidine- 2,4-dione (6). Whereas, cyclization of 9 with the reactive malonate ester 11 produced 3-[(5-butyl-4-hydroxy-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl) methylene]-1,5-diphenylpyrrolidine-2,4-dione (12). The condensation of some selected aromatic aldehydes 5a-c and addition of morpholine (7c) or piperidine (7d) to some of the resulting 3-arylidene-1,5-diphenylpyrrolidine-2,4-diones 13b, c gave the respective 3-substituted methyl-4-hydroxy-1,5-diphenyl-delta 3-pyrrolin-2-ones 14a-c. Selected members of the new series were screened for their in vitro antimicrobial, anti-HIV-1 and antineoplastic activities. Two compounds 14a, b showed pronounced inhibitory activities against Gram-positive bacteria; whereas, in the in vitro anti-HIV-1 screening, only one compound 13c displayed a moderate activity. However, in the antineoplastic screening protocol, the tested compounds were devoid of activity.
The syntheses of 3-chloro derivatives of 2-alkyl-pyrimido [1, 6-a] benzimidazol-1 (2H)-ones2a, b ... more The syntheses of 3-chloro derivatives of 2-alkyl-pyrimido [1, 6-a] benzimidazol-1 (2H)-ones2a, b as well as of 4, 4-dichloro and 4, 4-dibromo derivatives of 2-alkylpyrimido [1, 6-a] benzimidazole-1, 3 (2H, 4H)-diones3 a, b and4 are reported. Methods for converting some ...
The synthesis of some substituted 1, 3-dioxopyrimido [1, 6-a] benzimidazole-4-carbonitriles 6a, b... more The synthesis of some substituted 1, 3-dioxopyrimido [1, 6-a] benzimidazole-4-carbonitriles 6a, b and 4-ethyl carboxylates 6c, d through condensation of 1H-benzimidazole-2-acetonitriles 3a, b and ethyl 1H-benzimidazole-2-acetates 3c, d, respectively, with ...
The synthesis of some 3-substituted and 2, 3-disubstituted-1-oxo-1H, 5H-pyrido [1, 2-a] benzimida... more The synthesis of some 3-substituted and 2, 3-disubstituted-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbo-nitriles 5, 6 by fusing 1H-benzimidazole-2-acetonitrile 1 with some β-keto esters 2, 4 in the presence of ammonium acetate or with ethyl β- ...
The synthesis of some substituted 3-hydroxy-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbonit... more The synthesis of some substituted 3-hydroxy-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbonitriles and 4-ethyl carboxylates 3 and their 0-and N-dialkyl derivatives 5, 6 is described. 3-Ethoxy-5-ethyl-2-phenyl-1H, 5H-pyrido [1, 2-a] ...
The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-cJpyrrole-2,5-diones (5... more The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-cJpyrrole-2,5-diones (5) and 4-hydroxy-112,6,7-tetrahydro-5Hpyrrolo[3,4-b]pyridine-2,5-diones (6) by reacting li5-diaryl-pyrrolidine-2,4diones (1) and li5-diaryl-l,5-dihydro-4-amino-2H-pyrrol-2-ones (3) with bis-2,4,6-trichlorophenyl malonates (4) is described.
The fusion of 2-acetamidonicotinic acid witho-toluidine,p-bromoaniline oro-chloroaniline afforded... more The fusion of 2-acetamidonicotinic acid witho-toluidine,p-bromoaniline oro-chloroaniline afforded the corresponding 3-aryl-2-methyl-pyrido-[2,3-d]pyrimidin-4(3H)-ones (4), the 8-aza analogs of 3-aryl-2-methyl-4-quinazolinones, alongside 2-aminonicotinic acid. 2-Methyl-3-2(2-methylphenyl)-pyrido[2,3-d]pyrimidin-4(3H)-one (4a), the 8-aza analog of methaqualone, was converted to the 2-substituted styryl derivatives6 by condensation with some aromatic aldehydes and to the tricyclic system, 10-aza-5,6-dihydro-3-hydroxy-5-(2-methylphenyl)-2-substituted-1H-pyrido [1,2-a] quinazoline-1,6-diones (8) by reaction with monosubstituted bis-2,4,6-trichlorophenyl malonates.
Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4... more Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4H)-ones (10) are described. The first approach consists of cyclodehydrating 3(or 4)-hydroxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (4,7) with boiling acetic anhydride. The second approach involves cyclization of 3(or 4)-acetoxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (8,9) with elimination of acetic acid upon treatment with sodium hydroxide.
The synthesis of 2,5-disubstituted 5,6-dihydro-1 H-pyrido[1,2-a]quinazoline-1,6-diones (3) by rea... more The synthesis of 2,5-disubstituted 5,6-dihydro-1 H-pyrido[1,2-a]quinazoline-1,6-diones (3) by reacting monosubstituted bis 2,4,6-trichlorophenyl malonates (1) with 3-aryl-3,4- dihydro-2-methyl-4-quinazolinones (2) is described. Allylation of the pyridoquinazoline 3c with allylbromide afforded the corresponding 3-allyloxy derivative 4. Certain generalizations of the cleavage processes of this series in the MS are reported.
As a continuation of an earlier interest in polysubstituted pyrazoles, the synthesis of some deri... more As a continuation of an earlier interest in polysubstituted pyrazoles, the synthesis of some derivatives of 1H-pyrazol-4-yl-2-oxo-but-3-enoic acid and ethyl 4-hydroxy-1H-pyrazole-3-carboxylates of potential antimicrobial and antiinflammatory activity is described. One compound showed in vitro antibacterial activity and two compounds displayed in vivo antiinflammatory potency in rats.
The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethox... more The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethoxymethylene-1,5-diphenylpyrrolidine-2,4-dione (2). Reaction of the latter with hydrazine hydrate, secondary amines 7a-c or urea afforded the corresponding 3-substituted aminomethylene-1,5-diphenylpyrrolidene-2,4-diones 3, 8a-c or 9. On the other hand, condensation of 3 with veratraldehyde (5a) yielded 3-[(3,4-dimethoxybenzylidene)hydrazinomethylene]-1,5-diphenylpyrrolidine- 2,4-dione (6). Whereas, cyclization of 9 with the reactive malonate ester 11 produced 3-[(5-butyl-4-hydroxy-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl) methylene]-1,5-diphenylpyrrolidine-2,4-dione (12). The condensation of some selected aromatic aldehydes 5a-c and addition of morpholine (7c) or piperidine (7d) to some of the resulting 3-arylidene-1,5-diphenylpyrrolidine-2,4-diones 13b, c gave the respective 3-substituted methyl-4-hydroxy-1,5-diphenyl-delta 3-pyrrolin-2-ones 14a-c. Selected members of the new series wer...
The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethox... more The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethoxymethylene-1,5-diphenylpyrrolidine-2,4-dione (2). Reaction of the latter with hydrazine hydrate, secondary amines 7a-c or urea afforded the corresponding 3-substituted aminomethylene-1,5-diphenylpyrrolidene-2,4-diones 3, 8a-c or 9. On the other hand, condensation of 3 with veratraldehyde (5a) yielded 3-[(3,4-dimethoxybenzylidene)hydrazinomethylene]-1,5-diphenylpyrrolidine- 2,4-dione (6). Whereas, cyclization of 9 with the reactive malonate ester 11 produced 3-[(5-butyl-4-hydroxy-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl) methylene]-1,5-diphenylpyrrolidine-2,4-dione (12). The condensation of some selected aromatic aldehydes 5a-c and addition of morpholine (7c) or piperidine (7d) to some of the resulting 3-arylidene-1,5-diphenylpyrrolidine-2,4-diones 13b, c gave the respective 3-substituted methyl-4-hydroxy-1,5-diphenyl-delta 3-pyrrolin-2-ones 14a-c. Selected members of the new series were screened for their in vitro antimicrobial, anti-HIV-1 and antineoplastic activities. Two compounds 14a, b showed pronounced inhibitory activities against Gram-positive bacteria; whereas, in the in vitro anti-HIV-1 screening, only one compound 13c displayed a moderate activity. However, in the antineoplastic screening protocol, the tested compounds were devoid of activity.
The syntheses of 3-chloro derivatives of 2-alkyl-pyrimido [1, 6-a] benzimidazol-1 (2H)-ones2a, b ... more The syntheses of 3-chloro derivatives of 2-alkyl-pyrimido [1, 6-a] benzimidazol-1 (2H)-ones2a, b as well as of 4, 4-dichloro and 4, 4-dibromo derivatives of 2-alkylpyrimido [1, 6-a] benzimidazole-1, 3 (2H, 4H)-diones3 a, b and4 are reported. Methods for converting some ...
The synthesis of some substituted 1, 3-dioxopyrimido [1, 6-a] benzimidazole-4-carbonitriles 6a, b... more The synthesis of some substituted 1, 3-dioxopyrimido [1, 6-a] benzimidazole-4-carbonitriles 6a, b and 4-ethyl carboxylates 6c, d through condensation of 1H-benzimidazole-2-acetonitriles 3a, b and ethyl 1H-benzimidazole-2-acetates 3c, d, respectively, with ...
The synthesis of some 3-substituted and 2, 3-disubstituted-1-oxo-1H, 5H-pyrido [1, 2-a] benzimida... more The synthesis of some 3-substituted and 2, 3-disubstituted-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbo-nitriles 5, 6 by fusing 1H-benzimidazole-2-acetonitrile 1 with some β-keto esters 2, 4 in the presence of ammonium acetate or with ethyl β- ...
The synthesis of some substituted 3-hydroxy-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbonit... more The synthesis of some substituted 3-hydroxy-1-oxo-1H, 5H-pyrido [1, 2-a] benzimidazole-4-carbonitriles and 4-ethyl carboxylates 3 and their 0-and N-dialkyl derivatives 5, 6 is described. 3-Ethoxy-5-ethyl-2-phenyl-1H, 5H-pyrido [1, 2-a] ...
The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-cJpyrrole-2,5-diones (5... more The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-cJpyrrole-2,5-diones (5) and 4-hydroxy-112,6,7-tetrahydro-5Hpyrrolo[3,4-b]pyridine-2,5-diones (6) by reacting li5-diaryl-pyrrolidine-2,4diones (1) and li5-diaryl-l,5-dihydro-4-amino-2H-pyrrol-2-ones (3) with bis-2,4,6-trichlorophenyl malonates (4) is described.
The fusion of 2-acetamidonicotinic acid witho-toluidine,p-bromoaniline oro-chloroaniline afforded... more The fusion of 2-acetamidonicotinic acid witho-toluidine,p-bromoaniline oro-chloroaniline afforded the corresponding 3-aryl-2-methyl-pyrido-[2,3-d]pyrimidin-4(3H)-ones (4), the 8-aza analogs of 3-aryl-2-methyl-4-quinazolinones, alongside 2-aminonicotinic acid. 2-Methyl-3-2(2-methylphenyl)-pyrido[2,3-d]pyrimidin-4(3H)-one (4a), the 8-aza analog of methaqualone, was converted to the 2-substituted styryl derivatives6 by condensation with some aromatic aldehydes and to the tricyclic system, 10-aza-5,6-dihydro-3-hydroxy-5-(2-methylphenyl)-2-substituted-1H-pyrido [1,2-a] quinazoline-1,6-diones (8) by reaction with monosubstituted bis-2,4,6-trichlorophenyl malonates.
Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4... more Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4H)-ones (10) are described. The first approach consists of cyclodehydrating 3(or 4)-hydroxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (4,7) with boiling acetic anhydride. The second approach involves cyclization of 3(or 4)-acetoxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (8,9) with elimination of acetic acid upon treatment with sodium hydroxide.
The synthesis of 2,5-disubstituted 5,6-dihydro-1 H-pyrido[1,2-a]quinazoline-1,6-diones (3) by rea... more The synthesis of 2,5-disubstituted 5,6-dihydro-1 H-pyrido[1,2-a]quinazoline-1,6-diones (3) by reacting monosubstituted bis 2,4,6-trichlorophenyl malonates (1) with 3-aryl-3,4- dihydro-2-methyl-4-quinazolinones (2) is described. Allylation of the pyridoquinazoline 3c with allylbromide afforded the corresponding 3-allyloxy derivative 4. Certain generalizations of the cleavage processes of this series in the MS are reported.
As a continuation of an earlier interest in polysubstituted pyrazoles, the synthesis of some deri... more As a continuation of an earlier interest in polysubstituted pyrazoles, the synthesis of some derivatives of 1H-pyrazol-4-yl-2-oxo-but-3-enoic acid and ethyl 4-hydroxy-1H-pyrazole-3-carboxylates of potential antimicrobial and antiinflammatory activity is described. One compound showed in vitro antibacterial activity and two compounds displayed in vivo antiinflammatory potency in rats.
The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethox... more The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethoxymethylene-1,5-diphenylpyrrolidine-2,4-dione (2). Reaction of the latter with hydrazine hydrate, secondary amines 7a-c or urea afforded the corresponding 3-substituted aminomethylene-1,5-diphenylpyrrolidene-2,4-diones 3, 8a-c or 9. On the other hand, condensation of 3 with veratraldehyde (5a) yielded 3-[(3,4-dimethoxybenzylidene)hydrazinomethylene]-1,5-diphenylpyrrolidine- 2,4-dione (6). Whereas, cyclization of 9 with the reactive malonate ester 11 produced 3-[(5-butyl-4-hydroxy-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl) methylene]-1,5-diphenylpyrrolidine-2,4-dione (12). The condensation of some selected aromatic aldehydes 5a-c and addition of morpholine (7c) or piperidine (7d) to some of the resulting 3-arylidene-1,5-diphenylpyrrolidine-2,4-diones 13b, c gave the respective 3-substituted methyl-4-hydroxy-1,5-diphenyl-delta 3-pyrrolin-2-ones 14a-c. Selected members of the new series wer...
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