Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions
A regioselective N3-alkylation of 5,5-diphenyl-2-thiohydantoin (2-thiophenytoin) using a very efficient mild base K2CO3 and α,β-unsaturated esters in the presence of organic salt TBAB (tetrabutylammonium bromide) at room temperature has been reported (3b–3h). The selectivity of this reaction is exce...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2016-04-01
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| Series: | Green Chemistry Letters and Reviews |
| Subjects: | |
| Online Access: | http://dx.doi.org/10.1080/17518253.2016.1177606 |
| _version_ | 1819268256450478080 |
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| author | Gholamhassan Imanzadeh Aazam Aliabadi Mohammadreza Zamanloo |
| author_facet | Gholamhassan Imanzadeh Aazam Aliabadi Mohammadreza Zamanloo |
| author_sort | Gholamhassan Imanzadeh |
| collection | DOAJ |
| description | A regioselective N3-alkylation of 5,5-diphenyl-2-thiohydantoin (2-thiophenytoin) using a very efficient mild base K2CO3 and α,β-unsaturated esters in the presence of organic salt TBAB (tetrabutylammonium bromide) at room temperature has been reported (3b–3h). The selectivity of this reaction is excellent and products have been produced in good yields under solvent-free conditions. The increase of the reaction temperature to 70°C mostly disappeared this selectivity and afforded only the N1,N3-dialkylated derivatives of 2-thiophenytoin in good yields (4b–4g). We were unable to selectively N3-alkylate 2-thiophenytoin with ethyl acrylate at both room temperature and 70°C under the same conditions (4a). Dimethyl and diethyl fumarates cannot work as Michael acceptors and were hydrolyzed to fumaric acid under reaction conditions. |
| first_indexed | 2024-12-23T21:30:10Z |
| format | Article |
| id | doaj.art-c067e316f4c8443aa16f2d5d2f53bd87 |
| institution | Directory Open Access Journal |
| issn | 1751-8253 1751-7192 |
| language | English |
| last_indexed | 2024-12-23T21:30:10Z |
| publishDate | 2016-04-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Green Chemistry Letters and Reviews |
| spelling | doaj.art-c067e316f4c8443aa16f2d5d2f53bd872022-12-21T17:30:29ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922016-04-019210611310.1080/17518253.2016.11776061177606Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditionsGholamhassan Imanzadeh0Aazam Aliabadi1Mohammadreza Zamanloo2University of Mohaghegh ArdabiliUniversity of Mohaghegh ArdabiliUniversity of Mohaghegh ArdabiliA regioselective N3-alkylation of 5,5-diphenyl-2-thiohydantoin (2-thiophenytoin) using a very efficient mild base K2CO3 and α,β-unsaturated esters in the presence of organic salt TBAB (tetrabutylammonium bromide) at room temperature has been reported (3b–3h). The selectivity of this reaction is excellent and products have been produced in good yields under solvent-free conditions. The increase of the reaction temperature to 70°C mostly disappeared this selectivity and afforded only the N1,N3-dialkylated derivatives of 2-thiophenytoin in good yields (4b–4g). We were unable to selectively N3-alkylate 2-thiophenytoin with ethyl acrylate at both room temperature and 70°C under the same conditions (4a). Dimethyl and diethyl fumarates cannot work as Michael acceptors and were hydrolyzed to fumaric acid under reaction conditions.http://dx.doi.org/10.1080/17518253.2016.1177606Solvent-freeregioselectiveMichael addition2-thiophenytoinαβ-unsaturated esters |
| spellingShingle | Gholamhassan Imanzadeh Aazam Aliabadi Mohammadreza Zamanloo Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions Green Chemistry Letters and Reviews Solvent-free regioselective Michael addition 2-thiophenytoin α β-unsaturated esters |
| title | Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions |
| title_full | Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions |
| title_fullStr | Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions |
| title_full_unstemmed | Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions |
| title_short | Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions |
| title_sort | organic salt mediated highly regioselective n3 alkylation of 2 thiophenytoin via michael reaction under solvent free conditions |
| topic | Solvent-free regioselective Michael addition 2-thiophenytoin α β-unsaturated esters |
| url | http://dx.doi.org/10.1080/17518253.2016.1177606 |
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