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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| Published in | Journal of organic chemistry Vol. 84; no. 19; pp. 12573 - 12582 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
04.10.2019
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | De Castro, Pedro P Batista, Gabriel M. F Amarante, Giovanni W Dos Santos, Juliana A De Siqueira, Marcelo M Dos Santos, Hélio F |
| AuthorAffiliation | Chemistry Department |
| AuthorAffiliation_xml | – name: Chemistry Department |
| Author_xml | – sequence: 1 givenname: Pedro P surname: De Castro fullname: De Castro, Pedro P – sequence: 2 givenname: Juliana A surname: Dos Santos fullname: Dos Santos, Juliana A – sequence: 3 givenname: Marcelo M surname: De Siqueira fullname: De Siqueira, Marcelo M – sequence: 4 givenname: Gabriel M. F surname: Batista fullname: Batista, Gabriel M. F – sequence: 5 givenname: Hélio F orcidid: 0000-0003-0196-2642 surname: Dos Santos fullname: Dos Santos, Hélio F email: helio.santos@ufjf.edu.br – sequence: 6 givenname: Giovanni W orcidid: 0000-0003-1004-5395 surname: Amarante fullname: Amarante, Giovanni W email: giovanni.amarante@ufjf.edu.br |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31524388$$D View this record in MEDLINE/PubMed |
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| Keywords | CATALYSIS DESIGN OPTIMIZATION ISOXAZOL-5-ONES CONVERSION |
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| Title | Quantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones |
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