Preparation of 3,4-Substituted-5-Aminopyrazoles and 4
Substituted-2-Aminothiazoles

J 2018

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles

HAVEL, Štěpán, PrashantKumar KHIRSARIYA, Naresh AKAVARAM, Kamil PARUCH, Benoit Jean-Pierre CARBAIN et. al.

Základní údaje

Originální název

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles

Autoři

HAVEL, Štěpán (203 Česká republika, domácí), PrashantKumar KHIRSARIYA (356 Indie, domácí), Naresh AKAVARAM (356 Indie, domácí), Kamil PARUCH (203 Česká republika, domácí) a Benoit Jean-Pierre CARBAIN (250 Francie, garant, domácí)

Vydání

The Journal of Organic Chemistry, WASHINGTON, DC USA, American Chemical Society, 2018, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.745

Kód RIV

RIV/00216224:14310/18:00101515

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.8b02655

UT WoS

000454567900050

Klíčová slova česky

syntéza; medicinální chemie; stavební bloky; aminopyrazol; aminothiazol

Klíčová slova anglicky

synthesis; medicinal chemistry; building blocks; aminopyrazole; aminothiazole

Štítky

rivok

Změněno: 23. 4. 2024 13:03, Mgr. Michal Petr

Anotace

V originále

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated alfa-arylation of beta-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

Návaznosti

GJ16-23955Y, projekt VaV

Název: Nové a potentní inhibitory nukleázy MRE11 pro moderní výzkum rakoviny

Investor: Grantová agentura ČR, Novel efficient and selective inhibitors of MRE11 nuclease and their potential therapeutic implications

LM2015063, projekt VaV

Název: Národní infrastruktura chemické biologie (Akronym: CZ-OPENSCREEN)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CZ-OPENSCREEN: National Infrastructure for Chemical Biology

Citovat

HAVEL, Štěpán, PrashantKumar KHIRSARIYA, Naresh AKAVARAM, Kamil PARUCH a Benoit Jean-Pierre CARBAIN. Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles. The Journal of Organic Chemistry. WASHINGTON, DC USA: American Chemical Society, 2018, roč. 83, č. 24, s. 15380-15405. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.8b02655.

@article{1483842,
   author = {Havel, Štěpán and Khirsariya, PrashantKumar and Akavaram, Naresh and Paruch, Kamil and Carbain, Benoit JeanandPierre},
   article_location = {WASHINGTON, DC USA},
   article_number = {č. 24},
   doi = {http://dx.doi.org/10.1021/acs.joc.8b02655},
   keywords = {synthesis; medicinal chemistry; building blocks; aminopyrazole; aminothiazole},
   language = {eng},
   issn = {0022-3263},
   journal = {The Journal of Organic Chemistry},
   title = {Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles},
   url = {http://dx.doi.org/10.1021/acs.joc.8b02655},
   volume = {roč. 83},
   year = {2018}
}

TY  - JOUR
ID  - 1483842
AU  - Havel, Štěpán - Khirsariya, PrashantKumar - Akavaram, Naresh - Paruch, Kamil - Carbain, Benoit Jean-Pierre
PY  - 2018
TI  - Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles
JF  - The Journal of Organic Chemistry
VL  - roč. 83
IS  - č. 24
SP  - 15380-15405
EP  - 15380-15405
PB  - American Chemical Society
SN  - 00223263
KW  - synthesis
KW  - medicinal chemistry
KW  - building blocks
KW  - aminopyrazole
KW  - aminothiazole
UR  - http://dx.doi.org/10.1021/acs.joc.8b02655
N2  - 3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated alfa-arylation of beta-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.
ER  -

HAVEL, Štěpán, PrashantKumar KHIRSARIYA, Naresh AKAVARAM, Kamil PARUCH a Benoit Jean-Pierre CARBAIN. Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles. \textit{The Journal of Organic Chemistry}. WASHINGTON, DC USA: American Chemical Society, 2018, roč. 83, č. 24, s.~15380-15405. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.8b02655.

Podrobný výpis o publikaci