NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives
A chemoselective cascade cycloaddition reaction is developed for green and efficient access to cyclopenta[c]pyridine derivatives. Simple and inexpensive NaOH is used as the sole catalyst for this process. The δ-carbon of cyclopropyl ester is activated as a nucleophilic carbon to initiate highly chem...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/137826 |
| _version_ | 1811685331008749568 |
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| author | Pan, Dingwu Mou, Chengli Zan, Ningning Lv, Ya Song, Bao-An Chi, Robin Yonggui Jin, Zhichao |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Pan, Dingwu Mou, Chengli Zan, Ningning Lv, Ya Song, Bao-An Chi, Robin Yonggui Jin, Zhichao |
| author_sort | Pan, Dingwu |
| collection | NTU |
| description | A chemoselective cascade cycloaddition reaction is developed for green and efficient access to cyclopenta[c]pyridine derivatives. Simple and inexpensive NaOH is used as the sole catalyst for this process. The δ-carbon of cyclopropyl ester is activated as a nucleophilic carbon to initiate highly chemoselective cascade reactions. Cyclopenta[c]pyridines bearing various substituents are afforded in excellent yields. Preliminary studies on the bioactivities of the afforded products show promising antibacterial activities for potential applications in plant protections. |
| first_indexed | 2024-10-01T04:42:49Z |
| format | Journal Article |
| id | ntu-10356/137826 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:42:49Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1378262023-02-28T19:47:22Z NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives Pan, Dingwu Mou, Chengli Zan, Ningning Lv, Ya Song, Bao-An Chi, Robin Yonggui Jin, Zhichao School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Cycloaddition Chemoselective A chemoselective cascade cycloaddition reaction is developed for green and efficient access to cyclopenta[c]pyridine derivatives. Simple and inexpensive NaOH is used as the sole catalyst for this process. The δ-carbon of cyclopropyl ester is activated as a nucleophilic carbon to initiate highly chemoselective cascade reactions. Cyclopenta[c]pyridines bearing various substituents are afforded in excellent yields. Preliminary studies on the bioactivities of the afforded products show promising antibacterial activities for potential applications in plant protections. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-15T10:47:07Z 2020-04-15T10:47:07Z 2019 Journal Article Pan, D., Mou, C., Zan, N., Lv, Y., Song, B.-A., Chi, R. Y., & Jin, Z. (2019). NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives. Organic Letters, 21(17), 6624-6627. doi:10.1021/acs.orglett.9b02088 1523-7060 https://hdl.handle.net/10356/137826 10.1021/acs.orglett.9b02088 31411487 2-s2.0-85071653543 17 21 6624 6627 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b02088 application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Cycloaddition Chemoselective Pan, Dingwu Mou, Chengli Zan, Ningning Lv, Ya Song, Bao-An Chi, Robin Yonggui Jin, Zhichao NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title | NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title_full | NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title_fullStr | NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title_full_unstemmed | NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title_short | NaOH-promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines : access to bioactive cyclopenta[c]pyridine derivatives |
| title_sort | naoh promoted chemoselective cascade cyclization of cyclopropyl esters with unsaturated imines access to bioactive cyclopenta c pyridine derivatives |
| topic | Science::Chemistry::Organic chemistry Cycloaddition Chemoselective |
| url | https://hdl.handle.net/10356/137826 |
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