C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F14%3A10271953" target="_blank" >RIV/00216208:11310/14:10271953 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/14:00429665
Result on the web
<a href="http://dx.doi.org/10.3987/COM-14-12958" target="_blank" >http://dx.doi.org/10.3987/COM-14-12958</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3987/COM-14-12958" target="_blank" >10.3987/COM-14-12958</a>
Alternative languages
Result language
angličtina
Original language name
C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations
Original language description
Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5-(trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave thedesired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GAP207%2F12%2F0205" target="_blank" >GAP207/12/0205: Development of novel methodologies of C-H activations of purines, deazapurines, pyrimidines and related heterocycles</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Heterocycles
ISSN
0385-5414
e-ISSN
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Volume of the periodical
89
Issue of the periodical within the volume
5
Country of publishing house
JP - JAPAN
Number of pages
13
Pages from-to
1159-1171
UT code for WoS article
000336872600002
EID of the result in the Scopus database
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