Synthesis and application of alpha-carbonyl nitrile oxides

A novel strategy for synthesizing alpha-carbonyl nitrile oxides has been developed utilizingtert-butyl nitrite (TBN) as a nitrogen source. A diverse range of alpha-carbonyl furoxans and alpha-carbonyl isoxazoles have been obtained in good to excellent yields, including aromatic and aliphatic product...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 17; pp. 2467 - 2473
Main Authors Guo, Xuanhua, Xu, Guangqiang, Zhou, Li, Yan, Huating, Hao, Xin-Qi, Wang, Qinggang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.09.2020
Royal Society of Chemistry
Subjects
Aliphatic compounds
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Organic
Free radicals
Intermediates
Organic chemistry
Oxides
Physical Sciences
Science & Technology
FUROXAN
ALKENES
OXIMES
FACILE SYNTHESIS
ISOXAZOLE
TERT-BUTYL NITRITE
NITRATION
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Summary:A novel strategy for synthesizing alpha-carbonyl nitrile oxides has been developed utilizingtert-butyl nitrite (TBN) as a nitrogen source. A diverse range of alpha-carbonyl furoxans and alpha-carbonyl isoxazoles have been obtained in good to excellent yields, including aromatic and aliphatic products. The practical utility of this protocol has been demonstrated in gram-scale experiments and the syntheses of some bioactive molecules. A plausible free radical mechanism involving alpha-nitro ketone intermediates is proposed based on mechanistic investigations.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d0qo00780c