Application of Pd-Catalyzed Cross-Coupling Reactions in the
Synthesis of
5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that
inhibit ALK5 Kinase

J 2016

Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF, Milan POTÁČEK et. al.

Základní údaje

Originální název

Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase

Autoři

TENORA, Lukáš (203 Česká republika, domácí), Juraj GALETA (703 Slovensko, domácí), Eva ŘEZNÍČKOVÁ (203 Česká republika), Vladimír KRYŠTOF (203 Česká republika) a Milan POTÁČEK (203 Česká republika, garant, domácí)

Vydání

The Journal of Organic Chemistry, American Chemical Society, 2016, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.849

Kód RIV

RIV/00216224:14310/16:00091403

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.6b02230

UT WoS

000389396400032

Klíčová slova anglicky

Cross-Coupling reactions; Pd catalysed; 4H-pyrrolo[1;2-b]pyrazoles; ALK5 Kinase inhibitors;

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 3. 2017 10:15, Ing. Andrea Mikešková

Anotace

V originále

C-H activation of position 3 of a substituted pyrazole ring catalyzed by palladium(II) was straightforward and convenient for arylated or heteroarylated 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. Moreover, we introduced simple protection of the nitrogen in the pyridin-2-yl directing group, which otherwise does not allow cross-coupling reaction, by transformation to the N-oxide. Selected final products were reasonably selective ALK5 kinase inhibitors.

Citovat

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF a Milan POTÁČEK. Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase. The Journal of Organic Chemistry. American Chemical Society, 2016, roč. 81, č. 23, s. 11841-11856. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.6b02230.

@article{1358648,
   author = {Tenora, Lukáš and Galeta, Juraj and Řezníčková, Eva and Kryštof, Vladimír and Potáček, Milan},
   article_number = {23},
   doi = {http://dx.doi.org/10.1021/acs.joc.6b02230},
   keywords = {Cross-Coupling reactions; Pd catalysed; 4H-pyrrolo[1;2-b]pyrazoles; ALK5 Kinase inhibitors;},
   language = {eng},
   issn = {0022-3263},
   journal = {The Journal of Organic Chemistry},
   title = {Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230},
   volume = {81},
   year = {2016}
}

TY  - JOUR
ID  - 1358648
AU  - Tenora, Lukáš - Galeta, Juraj - Řezníčková, Eva - Kryštof, Vladimír - Potáček, Milan
PY  - 2016
TI  - Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase
JF  - The Journal of Organic Chemistry
VL  - 81
IS  - 23
SP  - 11841-11856
EP  - 11841-11856
PB  - American Chemical Society
SN  - 00223263
KW  - Cross-Coupling reactions
KW  - Pd catalysed
KW  - 4H-pyrrolo[1;2-b]pyrazoles
KW  - ALK5 Kinase inhibitors;
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230
N2  - C-H activation of position 3 of a substituted pyrazole ring catalyzed by palladium(II) was straightforward and convenient for arylated or heteroarylated 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. Moreover, we introduced simple protection of the nitrogen in the pyridin-2-yl directing group, which otherwise does not allow cross-coupling reaction, by transformation to the N-oxide. Selected final products were reasonably selective ALK5 kinase inhibitors.
ER  -

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF a Milan POTÁČEK. Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase. \textit{The Journal of Organic Chemistry}. American Chemical Society, 2016, roč.~81, č.~23, s.~11841-11856. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.6b02230.

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