tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

A sequential construction of C–C, C–O, CN, and CO bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc­(OTf)3 catalyst in DCE at 80 °C has been accomplished. An unprecedented three consecutive C–H functionalizations of two...

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Published inJournal of organic chemistry Vol. 82; no. 12; pp. 6358 - 6365
Main Authors Sau, Prasenjit, Santra, Sourav Kumar, Rakshit, Amitava, Patel, Bhisma K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
POTENTIAL ANTICANCER AGENTS
DIFUNCTIONALIZATION
ALCOHOLS
(BUONO)-BU-T
BIOLOGICAL EVALUATION
HYDROPEROXIDES
PEROXIDATION
ARYLBORONIC ACIDS
AEROBIC OXYNITRATION
NITRATION
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Summary:A sequential construction of C–C, C–O, CN, and CO bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc­(OTf)3 catalyst in DCE at 80 °C has been accomplished. An unprecedented three consecutive C–H functionalizations of two styrenes are involved in this isoxazoline synthesis. In this radical-mediated reaction, one-half of the aryl alkene is converted into an intermediate 2-nitroketone, which serves as a 1,3-dipolarophile and undergoes cycloaddition with the other half of the unreacted aromatic terminal alkene. The use of an alkyne in lieu of an alkene leads to the formation of isoxazole under identical reaction conditions.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00946