Polymer-assisted Synthesis of Single and Fused Diketomorpholines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F19%3A73596927" target="_blank" >RIV/61989592:15110/19:73596927 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/19:73596927
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00176" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00176</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acscombsci.8b00176" target="_blank" >10.1021/acscombsci.8b00176</a>
Alternative languages
Result language
angličtina
Original language name
Polymer-assisted Synthesis of Single and Fused Diketomorpholines
Original language description
The synthesis of different diketomorpholines via N-acyl-3,4-dihydro-2H-1,4-oxazine-3-carboxylic acids is reported in this article. The key intermediates were prepared using a convenient solid-phase synthesis starting from polymer-supported Ser(tBu)-OH. After subsequent sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), alkylation with an -bromoketone, cleavage of the 4-Nos group and acylation with an -halocarboxylic acids, acid-mediated cleavage from the resin yielded dihydrooxazine-3-carboxylic acids in high crude purities. Depending on the reaction conditions, exposure to base resulted in cyclization to either oxazino[3,4-c][1,4]oxazine-diones or 3-methylidenemorpholine-2,5-diones. Further reaction with triethylsilane-trifluoroacetic acid (TES-TFA) led to olefin reduction, in the case of oxazino[3,4-c][1,4]oxazine-dione with full control of the newly formed stereocenter.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/EF16_019%2F0000868" target="_blank" >EF16_019/0000868: Molecular, cellular and clinical approach to healthy ageing</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Combinatorial Science
ISSN
2156-8952
e-ISSN
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Volume of the periodical
21
Issue of the periodical within the volume
3
Country of publishing house
US - UNITED STATES
Number of pages
4
Pages from-to
154-157
UT code for WoS article
000461270400003
EID of the result in the Scopus database
2-s2.0-85062718066