Quantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones

The theoretical-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first experimental re...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 19; pp. 12573 - 12582
Main Authors De Castro, Pedro P, Dos Santos, Juliana A, De Siqueira, Marcelo M, Batista, Gabriel M. F, Dos Santos, Hélio F, Amarante, Giovanni W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.10.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
DESIGN
OPTIMIZATION
ISOXAZOL-5-ONES
CONVERSION
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Summary:The theoretical-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first experimental report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen– or carbon–acyloxy adducts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02099