C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61388963:_____/14:00429665

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F12%2F0205" target="_blank" >GAP207/12/0205: Vývoj nových metodik C-H aktivací purinů, deazapurinů, pyrimidinů a příbuzných heterocyklů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Heterocycles

ISSN

0385-5414

e-ISSN

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Svazek periodika

89

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

JP - Japonsko

Počet stran výsledku

13

Strana od-do

1159-1171

Kód UT WoS článku

000336872600002

EID výsledku v databázi Scopus

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