The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity
Reaction of 4-oxo-4-(3,4-dichlorophenyl)-2-butenoic acid (1) with antipyrin (2) gave the corresponding butanoic acid 3. Reaction of 3 with hydrazines gave the pyridazinone derivatives 5a,b. Compounds 5a,b were used to prepare the corresponding dithio derivatives. Reaction of 5a with POCl3 unexpected...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2003-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/8/3/322/ |
| _version_ | 1818176640682819584 |
|---|---|
| author | M. Shafik W. E. Boraie G. A. Meligi A. A. Hamed G. H. Sayed |
| author_facet | M. Shafik W. E. Boraie G. A. Meligi A. A. Hamed G. H. Sayed |
| author_sort | M. Shafik |
| collection | DOAJ |
| description | Reaction of 4-oxo-4-(3,4-dichlorophenyl)-2-butenoic acid (1) with antipyrin (2) gave the corresponding butanoic acid 3. Reaction of 3 with hydrazines gave the pyridazinone derivatives 5a,b. Compounds 5a,b were used to prepare the corresponding dithio derivatives. Reaction of 5a with POCl3 unexpectedly gave the chloropyridazine derivative 7, which is used to prepare the corresponding thio derivative. The hitherto unknown reactions of this chloro derivative with 2-amino-3-carbethoxy-4,5-dimethylthiophene and 2-amino-3-carbethoxy tetrahydrobenzothiophene have now been described. The behaviour of the chloro derivative toward hydrazine hydrate, sodium azide and anthranilic acid was also studied. Some of the new compounds showed antimicrobial and antifungal activities . |
| first_indexed | 2024-12-11T20:19:24Z |
| format | Article |
| id | doaj.art-293b55542e2149789ce907158a23b457 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T20:19:24Z |
| publishDate | 2003-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-293b55542e2149789ce907158a23b4572022-12-22T00:52:07ZengMDPI AGMolecules1420-30492003-03-018332233210.3390/80300322The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological ActivityM. ShafikW. E. BoraieG. A. MeligiA. A. HamedG. H. SayedReaction of 4-oxo-4-(3,4-dichlorophenyl)-2-butenoic acid (1) with antipyrin (2) gave the corresponding butanoic acid 3. Reaction of 3 with hydrazines gave the pyridazinone derivatives 5a,b. Compounds 5a,b were used to prepare the corresponding dithio derivatives. Reaction of 5a with POCl3 unexpectedly gave the chloropyridazine derivative 7, which is used to prepare the corresponding thio derivative. The hitherto unknown reactions of this chloro derivative with 2-amino-3-carbethoxy-4,5-dimethylthiophene and 2-amino-3-carbethoxy tetrahydrobenzothiophene have now been described. The behaviour of the chloro derivative toward hydrazine hydrate, sodium azide and anthranilic acid was also studied. Some of the new compounds showed antimicrobial and antifungal activities .http://www.mdpi.com/1420-3049/8/3/322/Substituted pyridazinoneschloropyridazinesubstituted thiophenes |
| spellingShingle | M. Shafik W. E. Boraie G. A. Meligi A. A. Hamed G. H. Sayed The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity Molecules Substituted pyridazinones chloropyridazine substituted thiophenes |
| title | The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity |
| title_full | The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity |
| title_fullStr | The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity |
| title_full_unstemmed | The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity |
| title_short | The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity |
| title_sort | use of 4 3 4 dichlorophenyl 4 oxo 2 4 antipyrinyl butanoic acid in the preparation of some new heterocyclic compounds with expected biological activity |
| topic | Substituted pyridazinones chloropyridazine substituted thiophenes |
| url | http://www.mdpi.com/1420-3049/8/3/322/ |
| work_keys_str_mv | AT mshafik theuseof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT weboraie theuseof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT gameligi theuseof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT aahamed theuseof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT ghsayed theuseof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT mshafik useof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT weboraie useof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT gameligi useof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT aahamed useof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity AT ghsayed useof434dichlorophenyl4oxo24antipyrinylbutanoicacidinthepreparationofsomenewheterocycliccompoundswithexpectedbiologicalactivity |