Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles
The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-bute...
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| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2020-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2020/5945796 |
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| author | Hassan Kabirifard Pardis Hafez Taghva Hossein Teimouri Niloofar Koosheshi Parastoo Javadpour Hanieh Bagherinejad Soheila Seyfi Maryam Hossein Roodbari Elaheh Golabian |
| author_facet | Hassan Kabirifard Pardis Hafez Taghva Hossein Teimouri Niloofar Koosheshi Parastoo Javadpour Hanieh Bagherinejad Soheila Seyfi Maryam Hossein Roodbari Elaheh Golabian |
| author_sort | Hassan Kabirifard |
| collection | DOAJ |
| description | The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes. |
| format | Article |
| id | doaj-art-592f0c2776a340b8958df60e017c5c79 |
| institution | Kabale University |
| issn | 1042-7163 1098-1071 |
| language | English |
| publishDate | 2020-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-592f0c2776a340b8958df60e017c5c792025-02-03T06:45:53ZengWileyHeteroatom Chemistry1042-71631098-10712020-01-01202010.1155/2020/59457965945796Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-NucleophilesHassan Kabirifard0Pardis Hafez Taghva1Hossein Teimouri2Niloofar Koosheshi3Parastoo Javadpour4Hanieh Bagherinejad5Soheila Seyfi6Maryam Hossein Roodbari7Elaheh Golabian8Department of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, IranThe reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.http://dx.doi.org/10.1155/2020/5945796 |
| spellingShingle | Hassan Kabirifard Pardis Hafez Taghva Hossein Teimouri Niloofar Koosheshi Parastoo Javadpour Hanieh Bagherinejad Soheila Seyfi Maryam Hossein Roodbari Elaheh Golabian Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles Heteroatom Chemistry |
| title | Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles |
| title_full | Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles |
| title_fullStr | Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles |
| title_full_unstemmed | Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles |
| title_short | Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles |
| title_sort | synthesis of organic ligands via reactions of 4 benzoyl 5 phenylamino 2 3 dihydrothiophene 2 3 dione with n nucleophiles |
| url | http://dx.doi.org/10.1155/2020/5945796 |
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