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

ABSTRACT: 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.

SUBMITTER: Cao JK 

PROVIDER: S-EPMC10974807 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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

Cao Jian-Kang JK   Cao Tian-Zheng TZ   Yue Qian-Wen QW   Ma Ying Y   Yang Chuan-Ming CM   Zhang Hong-Xi HX   Li Ya-Chen YC   Dong Qiao-Ke QK   Zhu Yan-Ping YP   Sun Yuan-Yuan YY  

Molecules (Basel, Switzerland) 20240307 6

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</sub><sup>3</sup>-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 usin  ...[more]

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