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-...

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Main Authors: Kuo Wang, Yue Zhang, Lu-Yu Cai, Xiu-Qing Song, Chen Wang, Jia-Rui Zhang, Yi-Fan Pan, Hong-Wu Zhao
Format: Article
Language:English
Published: MDPI AG 2023-10-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/20/7021
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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.
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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
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