Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines
Under the catalysis of Rh<sub>2</sub>(OAc)<sub>4</sub> (10 mol%) and binapbisphosphine ligand (±)-<b>L3</b> (20 mol%) in DCE at 80 °C, the cascade cyclization of diazoimides with alkylidenepyrazolones underwent stereoselectively (dr > 20:1), affording pyrazole-...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-10-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/20/7021 |
| _version_ | 1827720310986637312 |
|---|---|
| author | Kuo Wang Yue Zhang Lu-Yu Cai Xiu-Qing Song Chen Wang Jia-Rui Zhang Yi-Fan Pan Hong-Wu Zhao |
| author_facet | Kuo Wang Yue Zhang Lu-Yu Cai Xiu-Qing Song Chen Wang Jia-Rui Zhang Yi-Fan Pan Hong-Wu Zhao |
| author_sort | Kuo Wang |
| collection | DOAJ |
| description | Under the catalysis of Rh<sub>2</sub>(OAc)<sub>4</sub> (10 mol%) and binapbisphosphine ligand (±)-<b>L3</b> (20 mol%) in DCE at 80 °C, the cascade cyclization of diazoimides with alkylidenepyrazolones underwent stereoselectively (dr > 20:1), affording pyrazole-fused oxa-bridged oxazocines in reasonable chemical yields. The chemical structure and relative configuration of title products were firmly identified by X-ray diffraction analysis. |
| first_indexed | 2024-03-10T21:00:36Z |
| format | Article |
| id | doaj.art-573c0b1a1ad04029ab0bc2b6f11bf5a4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:00:36Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-573c0b1a1ad04029ab0bc2b6f11bf5a42023-11-19T17:31:35ZengMDPI AGMolecules1420-30492023-10-012820702110.3390/molecules28207021Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged OxazocinesKuo Wang0Yue Zhang1Lu-Yu Cai2Xiu-Qing Song3Chen Wang4Jia-Rui Zhang5Yi-Fan Pan6Hong-Wu Zhao7College of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaCollege of Life Science and Bio-Engineering, Beijing University of Technology, No.100 Pingleyuan, Chaoyang District, Beijing 100124, ChinaUnder the catalysis of Rh<sub>2</sub>(OAc)<sub>4</sub> (10 mol%) and binapbisphosphine ligand (±)-<b>L3</b> (20 mol%) in DCE at 80 °C, the cascade cyclization of diazoimides with alkylidenepyrazolones underwent stereoselectively (dr > 20:1), affording pyrazole-fused oxa-bridged oxazocines in reasonable chemical yields. The chemical structure and relative configuration of title products were firmly identified by X-ray diffraction analysis.https://www.mdpi.com/1420-3049/28/20/7021diastereoselectivitycascade cyclizationdiazoimidealkylidenepyrazoloneoxazocine |
| spellingShingle | Kuo Wang Yue Zhang Lu-Yu Cai Xiu-Qing Song Chen Wang Jia-Rui Zhang Yi-Fan Pan Hong-Wu Zhao Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines Molecules diastereoselectivity cascade cyclization diazoimide alkylidenepyrazolone oxazocine |
| title | Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines |
| title_full | Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines |
| title_fullStr | Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines |
| title_full_unstemmed | Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines |
| title_short | Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines |
| title_sort | diastereoselective cascade cyclization of diazoimides with alkylidene pyrazolones for preparation of pyrazole fused oxa bridged oxazocines |
| topic | diastereoselectivity cascade cyclization diazoimide alkylidenepyrazolone oxazocine |
| url | https://www.mdpi.com/1420-3049/28/20/7021 |
| work_keys_str_mv | AT kuowang diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT yuezhang diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT luyucai diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT xiuqingsong diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT chenwang diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT jiaruizhang diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT yifanpan diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines AT hongwuzhao diastereoselectivecascadecyclizationofdiazoimideswithalkylidenepyrazolonesforpreparationofpyrazolefusedoxabridgedoxazocines |