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Itert/I-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones

Molecules (Basel, Switzerland), 2024-03, Vol.29 (6) [Peer Reviewed Journal]

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Title:
Itert/I-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones
Author: Cao, Jian-Kang ; Cao, Tian-Zheng ; Yue, Qian-Wen ; Ma, Ying ; Yang, Chuan-Ming ; Zhang, Hong-Xi ; Li, Ya-Chen ; Dong, Qiao-Ke ; Zhu, Yan-Ping ; Sun, Yuan-Yuan
Subjects: Ketones ; Oxidation-reduction reaction
Is Part Of: Molecules (Basel, Switzerland), 2024-03, Vol.29 (6)
Description: A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through C[sub.sp] [sup.3]–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor.
Publisher: MDPI AG
Language: English
Identifier: ISSN: 1420-3049
EISSN: 1420-3049
DOI: 10.3390/molecules29061202
Source: Geneva Foundation Free Medical Journals at publisher websites
PubMed Central
Alma/SFX Local Collection
ProQuest Central
DOAJ Directory of Open Access Journals

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