Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes
As a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline der...
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| Format: | Article |
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Frontiers Media S.A.
2021-11-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.764866/full |
| _version_ | 1819118276053041152 |
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| author | Taiwei Dong Peifeng Wei Min Li Feng Gao Yuan Qin |
| author_facet | Taiwei Dong Peifeng Wei Min Li Feng Gao Yuan Qin |
| author_sort | Taiwei Dong |
| collection | DOAJ |
| description | As a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline derivatives has been successfully achieved. This strategy proceeds efficiently under mild condition, offering straightforward route to a variety of 4-aryl-substituted tetrahydroquinolines with high yields, excellent diastereoselectivities, broad functional group tolerance as well as gram-scale capacity. Moreover, a one-pot reaction sequence utilizing in situ generated p-QMs under the similar condition to build tetrahydroquinoline framework is smoothly conducted with good reaction performance as well as step and atom economy. |
| first_indexed | 2024-12-22T05:46:18Z |
| format | Article |
| id | doaj.art-b00561f22d5c40f2abc346de2a42e589 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T05:46:18Z |
| publishDate | 2021-11-01 |
| publisher | Frontiers Media S.A. |
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| series | Frontiers in Chemistry |
| spelling | doaj.art-b00561f22d5c40f2abc346de2a42e5892022-12-21T18:37:00ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-11-01910.3389/fchem.2021.764866764866Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and CyanoalkenesTaiwei Dong0Peifeng Wei1Min Li2Feng Gao3Yuan Qin4College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, ChinaCollege of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, ChinaCollege of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, ChinaCollege of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, ChinaState Key Laboratory of Military Stomatology and National Clinical Research Center for Oral Diseases and Shaanxi Clinical Research Center for Oral Diseases, Department of Orthodontics, School of Stomatology, The Fourth Military Medical University, Xi’an, ChinaAs a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline derivatives has been successfully achieved. This strategy proceeds efficiently under mild condition, offering straightforward route to a variety of 4-aryl-substituted tetrahydroquinolines with high yields, excellent diastereoselectivities, broad functional group tolerance as well as gram-scale capacity. Moreover, a one-pot reaction sequence utilizing in situ generated p-QMs under the similar condition to build tetrahydroquinoline framework is smoothly conducted with good reaction performance as well as step and atom economy.https://www.frontiersin.org/articles/10.3389/fchem.2021.764866/fulltetrahydroquinolinesp-quinone methidesmulti-substituted alkenesAza-Michael16-conjugate addition |
| spellingShingle | Taiwei Dong Peifeng Wei Min Li Feng Gao Yuan Qin Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes Frontiers in Chemistry tetrahydroquinolines p-quinone methides multi-substituted alkenes Aza-Michael 1 6-conjugate addition |
| title | Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes |
| title_full | Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes |
| title_fullStr | Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes |
| title_full_unstemmed | Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes |
| title_short | Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes |
| title_sort | highly diastereoselective synthesis of tetrahydroquinoline derivatives via 4 2 annulation of ortho tosylaminophenyl substituted para quinone methides and cyanoalkenes |
| topic | tetrahydroquinolines p-quinone methides multi-substituted alkenes Aza-Michael 1 6-conjugate addition |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.764866/full |
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