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

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 Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 6; p. 1202
Main Authors 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
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 07.03.2024
MDPI
Subjects
aryl methyl ketones
Chemical bonds
Chromatography
intramolecular cycloaddition
Investigations
isoxazole/isoxazoline
Natural products
Oxidation
polycyclic architectures
tert-butyl nitrite (TBN)
isoxazole/isoxazoline
intramolecular cycloaddition
polycyclic architectures
aryl methyl ketones
tert-butyl nitrite (TBN)
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Summary: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 Csp3–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.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29061202