Microwave assisted synthesis of novel functionalized hydantoin derivatives and their conversion to 5-(Z) arylidene-4H-imidazoles
2-(Alkyl-1-yl)-1H-imidazol-5(4H)-ones 5a-n were synthesized via nucleophilic substitution of the methylsulfanyl group of the corresponding 2-(methylthio)-1H-imidazol-5(4H)-ones 3a-c with suitably substituted secondary amines. The starting 2-thioxo- imidazolidin-4-ones 2a,2b were prepared by condensa...
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| Published in: | Molecules (Basel, Switzerland) Vol. 16; no. 7; pp. 5527 - 5537 |
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| Abstract | 2-(Alkyl-1-yl)-1H-imidazol-5(4H)-ones 5a-n were synthesized via nucleophilic substitution of the methylsulfanyl group of the corresponding 2-(methylthio)-1H-imidazol-5(4H)-ones 3a-c with suitably substituted secondary amines. The starting 2-thioxo- imidazolidin-4-ones 2a,2b were prepared by condensation of thiohydantoin and benzo[b]-thiophene-3-carbaldehyde or benzofuran-3-carbaldehyde under microwave irracdiation (MW) conditions. 2-Methylthio derivatives 3a-c were prepared by treatment of 2a-b with methyl iodide in the presence of aqueous sodium hydroxide. |
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| AbstractList | 2-(Alkyl-1-yl)-1H-imidazol-5(4H)-ones 5a–n were synthesized via nucleophilic substitution of the methylsulfanyl group of the corresponding 2-(methylthio)-1H-imidazol-5(4H)-ones 3a–c with suitably substituted secondary amines. The starting 2-thioxo- imidazolidin-4-ones 2a,2b were prepared by condensation of thiohydantoin and benzo[b]-thiophene-3-carbaldehyde or benzofuran-3-carbaldehyde under microwave irracdiation (MW) conditions. 2-Methylthio derivatives 3a–c were prepared by treatment of 2a–b with methyl iodide in the presence of aqueous sodium hydroxide. 2-(Alkyl-1-yl)-1 H -imidazol-5(4 H) -ones 5a–n were synthesized via nucleophilic substitution of the methylsulfanyl group of the corresponding 2-(methylthio)-1 H -imidazol-5(4 H )-ones 3a–c with suitably substituted secondary amines. The starting 2-thioxo- imidazolidin-4-ones 2a , 2b were prepared by condensation of thiohydantoin and benzo[ b ]-thiophene-3-carbaldehyde or benzofuran-3-carbaldehyde under microwave irracdiation (MW) conditions. 2-Methylthio derivatives 3a–c were prepared by treatment of 2a–b with methyl iodide in the presence of aqueous sodium hydroxide. |
| Author | Biehl, Edward R Ankati, Haribabu Kamila, Sukanta |
| AuthorAffiliation | Department of Chemistry, Southern Methodist University, 3215 Daniel Avenue, Dallas, TX 75275, USA |
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| Author_xml | – sequence: 1 givenname: Sukanta surname: Kamila fullname: Kamila, Sukanta organization: Department of Chemistry, Southern Methodist University, 3215 Daniel Avenue, Dallas, TX 75275, USA – sequence: 2 givenname: Haribabu surname: Ankati fullname: Ankati, Haribabu – sequence: 3 givenname: Edward R surname: Biehl fullname: Biehl, Edward R |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21716174$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2014_05_038 crossref_primary_10_1016_j_tetlet_2012_05_088 crossref_primary_10_3987_COM_13_S_S_36 crossref_primary_10_1016_j_ejmech_2014_11_061 crossref_primary_10_1016_j_tetlet_2012_08_093 crossref_primary_10_1016_j_tetlet_2012_06_116 crossref_primary_10_1016_j_tetlet_2012_02_064 |
| Cites_doi | 10.1016/S1359-6101(99)00005-2 10.1002/cber.19821150340 10.1097/00001813-199611000-00009 10.1016/S0014-2999(03)02179-4 10.1080/00397910903243823 10.1097/01.ALC.0000134412.38510.F7 10.1002/jnr.22352 10.1016/S0079-6468(08)70120-6 10.1021/jm00027a009 10.3987/COM-00-9143 10.3181/0805-RM-153 10.1080/00397910500514071 |
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| DOI | 10.3390/molecules16075527 |
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| SubjectTerms | arylidene-4H-imidazoles Ethanol hydantoin Hydantoins - chemical synthesis Hydantoins - chemistry Imidazoles - chemical synthesis Imidazoles - chemistry Magnetic Resonance Spectroscopy Microwaves Molecular Structure MW assisted synthesis Solvents Thiohydantoins - chemical synthesis Thiohydantoins - chemistry |
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| Title | Microwave assisted synthesis of novel functionalized hydantoin derivatives and their conversion to 5-(Z) arylidene-4H-imidazoles |
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