Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and...
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MDPI AG
2022-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/10/3064 |
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| author | Kaikai Wang Yanli Li Wei Zhang Rongxiang Chen Xueji Ma Mingyue Wang Nan Zhou |
| author_facet | Kaikai Wang Yanli Li Wei Zhang Rongxiang Chen Xueji Ma Mingyue Wang Nan Zhou |
| author_sort | Kaikai Wang |
| collection | DOAJ |
| description | A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process. |
| first_indexed | 2024-03-10T03:21:20Z |
| format | Article |
| id | doaj.art-a0b33732ab00475f834765c38364cd15 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:21:20Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a0b33732ab00475f834765c38364cd152023-11-23T12:20:25ZengMDPI AGMolecules1420-30492022-05-012710306410.3390/molecules27103064Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline IminesKaikai Wang0Yanli Li1Wei Zhang2Rongxiang Chen3Xueji Ma4Mingyue Wang5Nan Zhou6School of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaMedical College, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaA mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process.https://www.mdpi.com/1420-3049/27/10/30641,2,4-oxadiazolinesoxime chloridescycloadditioncyclic imines |
| spellingShingle | Kaikai Wang Yanli Li Wei Zhang Rongxiang Chen Xueji Ma Mingyue Wang Nan Zhou Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines Molecules 1,2,4-oxadiazolines oxime chlorides cycloaddition cyclic imines |
| title | Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines |
| title_full | Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines |
| title_fullStr | Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines |
| title_full_unstemmed | Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines |
| title_short | Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines |
| title_sort | facile synthesis of tricyclic 1 2 4 oxadiazolines fused tetrahydro isoquinolines from oxime chlorides with 3 4 dihydroisoquinoline imines |
| topic | 1,2,4-oxadiazolines oxime chlorides cycloaddition cyclic imines |
| url | https://www.mdpi.com/1420-3049/27/10/3064 |
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