One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and alpha-bromoketones
A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-, isothio-or isoselenocyanates, and alpha-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one interm...
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| Published in | Organic & biomolecular chemistry Vol. 17; no. 11; pp. 3040 - 3047 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
13.03.2019
Royal Society of Chemistry |
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| Abstract | A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-, isothio-or isoselenocyanates, and alpha-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones. |
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| AbstractList | A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from
l
-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones. A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones. A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-, isothio-or isoselenocyanates, and alpha-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones. |
| Author | Haung, Jia-Yun Barve, Indrajeet J. Sun, Chung-Ming |
| Author_xml | – sequence: 1 givenname: Jia-Yun surname: Haung fullname: Haung, Jia-Yun organization: Natl Chiao Tung Univ, Dept Appl Chem, 1001 Ta Hseuh Rd, Hsinchu 30010, Taiwan – sequence: 2 givenname: Indrajeet J. orcidid: 0000-0002-2164-9621 surname: Barve fullname: Barve, Indrajeet J. organization: Natl Chiao Tung Univ, Dept Appl Chem, 1001 Ta Hseuh Rd, Hsinchu 30010, Taiwan – sequence: 3 givenname: Chung-Ming surname: Sun fullname: Sun, Chung-Ming email: cmsun@nctu.edu.tw organization: Natl Chiao Tung Univ, Dept Appl Chem, 1001 Ta Hseuh Rd, Hsinchu 30010, Taiwan |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30816898$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1002/slct.201801349 10.1080/14786410802270738 10.1002/chem.201600602 10.1021/ja710388h 10.1080/1057563031000072613 10.1016/j.bioorg.2017.04.002 10.1016/j.tetlet.2009.04.036 10.1021/jo501922j 10.1021/cr010142r 10.1039/b503848k 10.1002/slct.201801288 10.1016/j.bioorg.2007.12.003 10.1016/S0040-4039(98)01031-4 10.1039/cs9972600443 10.2174/157018009787158553 10.1039/B503848K 10.1016/0378-1119(92)90691-H 10.1016/0040-4020(95)00321-X 10.1038/nbt1097-961 |
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| Keywords | GFP GREEN FLUORESCENT PROTEIN ULTRASOUND CHROMOPHORES KAEDE |
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| Snippet | A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-,... A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio-... A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from l -amino acid methyl esters, iso-,... |
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| SubjectTerms | Acids Amino acids Chemical synthesis Chemistry Chemistry, Organic Crystallography Esters High-performance liquid chromatography Intermediates Isocyanates Liquid chromatography NMR Nuclear magnetic resonance Physical Sciences Reaction mechanisms Science & Technology |
| Title | One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and alpha-bromoketones |
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