1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary a...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2013
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| Online Access: | https://hdl.handle.net/10356/105286 http://hdl.handle.net/10220/16575 http://dx.doi.org/10.1002/chem.201202606 |
| _version_ | 1826118597435457536 |
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| author | Kothandaraman, Prasath Koh, Bing Qin Limpanuparb, Taweetham Hirao, Hajime Chan, Philip Wai Hong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Kothandaraman, Prasath Koh, Bing Qin Limpanuparb, Taweetham Hirao, Hajime Chan, Philip Wai Hong |
| author_sort | Kothandaraman, Prasath |
| collection | NTU |
| description | A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. |
| first_indexed | 2024-10-01T04:46:06Z |
| format | Journal Article |
| id | ntu-10356/105286 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:46:06Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/1052862019-12-06T21:48:47Z 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis Kothandaraman, Prasath Koh, Bing Qin Limpanuparb, Taweetham Hirao, Hajime Chan, Philip Wai Hong School of Physical and Mathematical Sciences A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. 2013-10-18T02:28:15Z 2019-12-06T21:48:47Z 2013-10-18T02:28:15Z 2019-12-06T21:48:47Z 2013 2013 Journal Article Kothandaraman, P., Koh, B. Q., Limpanuparb, T., Hirao, H.,& Chan, P. W. H. (2013). 1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis. Chemistry - A European Journal, 19(6), 1978-1985. 0947-6539 https://hdl.handle.net/10356/105286 http://hdl.handle.net/10220/16575 http://dx.doi.org/10.1002/chem.201202606 en Chemistry - a European journal |
| spellingShingle | Kothandaraman, Prasath Koh, Bing Qin Limpanuparb, Taweetham Hirao, Hajime Chan, Philip Wai Hong 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title | 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title_full | 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title_fullStr | 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title_full_unstemmed | 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title_short | 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis |
| title_sort | 1 2 anilinyl prop 2 yn 1 ol rearrangement for oxindole synthesis |
| url | https://hdl.handle.net/10356/105286 http://hdl.handle.net/10220/16575 http://dx.doi.org/10.1002/chem.201202606 |
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