Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid
In this work pyrazolin derivatives were prepared from the diazonium chloride salt of 4-aminobenzoic acid. Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, acetyl acetone to obtain the corresponding hy...
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| Format: | Article |
| Language: | Arabic |
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College of Science for Women, University of Baghdad
2010-03-01
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| Series: | Baghdad Science Journal |
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| Online Access: | http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2916 |
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| author | Baghdad Science Journal |
| author_facet | Baghdad Science Journal |
| author_sort | Baghdad Science Journal |
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| description | In this work pyrazolin derivatives were prepared from the diazonium chloride salt of 4-aminobenzoic acid. Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, acetyl acetone to obtain the corresponding hydrazono derivative (1). Cyclocondensation reaction of compounds (1) with hydrazine hydrate and phenyl hydrazine in boiling ethanol affording the corresponding pyrazoline-5-one derivatives of 4-aminobenzoic acid (2,3). Then compound (3) was reacted with thionyl chloride to give the corresponding acid chloride derivative(4), followed by conversion into the corresponding acid hydrazide derivative (5) carboxylic acid thiosemicarbazide (11), esters (14,15), thioesters (16,17) and amides (18,19), when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry refluxing benzene; respectively. Schiff's bases (6-8) were prepared by refluxing of compound (5) with different aldehydes and ketons, then two compounds from the Schiff's bases were cyclized with ?-mercapto acetic acid to give (9 and 10). Furthermore, 1,2,4-triazole derivative (12) have been also prepared by refluxing thiosemicarbazide derivative with sodium hydroxide solution (4%) followed acidification of the result using (10%)hydrolic acid. Moreover, a thiadiazole derivative (13) has been prepared by treatment of thiosemicarbazide derivative with concentrated sulfuric acid as cyclyzing agent. Finally, oxadiazole derivative (20) has prepared by condensation of its acid hydrazide derivative with carbon disulfide in basic medium. |
| first_indexed | 2024-12-10T18:45:19Z |
| format | Article |
| id | doaj.art-481eb6bf389f45109aed53a5e262ce30 |
| institution | Directory Open Access Journal |
| issn | 2078-8665 2411-7986 |
| language | Arabic |
| last_indexed | 2024-12-10T18:45:19Z |
| publishDate | 2010-03-01 |
| publisher | College of Science for Women, University of Baghdad |
| record_format | Article |
| series | Baghdad Science Journal |
| spelling | doaj.art-481eb6bf389f45109aed53a5e262ce302022-12-22T01:37:31ZaraCollege of Science for Women, University of BaghdadBaghdad Science Journal2078-86652411-79862010-03-017110.21123/bsj.7.1.727-736Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acidBaghdad Science JournalIn this work pyrazolin derivatives were prepared from the diazonium chloride salt of 4-aminobenzoic acid. Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, acetyl acetone to obtain the corresponding hydrazono derivative (1). Cyclocondensation reaction of compounds (1) with hydrazine hydrate and phenyl hydrazine in boiling ethanol affording the corresponding pyrazoline-5-one derivatives of 4-aminobenzoic acid (2,3). Then compound (3) was reacted with thionyl chloride to give the corresponding acid chloride derivative(4), followed by conversion into the corresponding acid hydrazide derivative (5) carboxylic acid thiosemicarbazide (11), esters (14,15), thioesters (16,17) and amides (18,19), when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry refluxing benzene; respectively. Schiff's bases (6-8) were prepared by refluxing of compound (5) with different aldehydes and ketons, then two compounds from the Schiff's bases were cyclized with ?-mercapto acetic acid to give (9 and 10). Furthermore, 1,2,4-triazole derivative (12) have been also prepared by refluxing thiosemicarbazide derivative with sodium hydroxide solution (4%) followed acidification of the result using (10%)hydrolic acid. Moreover, a thiadiazole derivative (13) has been prepared by treatment of thiosemicarbazide derivative with concentrated sulfuric acid as cyclyzing agent. Finally, oxadiazole derivative (20) has prepared by condensation of its acid hydrazide derivative with carbon disulfide in basic medium.http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2916"Azo compound, Pyrazol derivatives, active methylene compound" |
| spellingShingle | Baghdad Science Journal Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid Baghdad Science Journal "Azo compound, Pyrazol derivatives, active methylene compound" |
| title | Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid |
| title_full | Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid |
| title_fullStr | Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid |
| title_full_unstemmed | Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid |
| title_short | Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid |
| title_sort | synthesis of new heterocyclic derivatives from 4 3 5 dimethyl 1 phenyl 1h pyrazol 4 ylazo benzoic acid |
| topic | "Azo compound, Pyrazol derivatives, active methylene compound" |
| url | http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2916 |
| work_keys_str_mv | AT baghdadsciencejournal synthesisofnewheterocyclicderivativesfrom435dimethyl1phenyl1hpyrazol4ylazobenzoicacid |