One-pot method for the synthesis of 1-aryl-2-aminoalkanol
derivatives from the corresponding amides or nitriles

J 2020

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

OTEVŘEL, Jan, David ŠVESTKA a Pavel BOBÁĽ

Základní údaje

Originální název

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

Autoři

OTEVŘEL, Jan (203 Česká republika, garant, domácí), David ŠVESTKA (203 Česká republika, domácí) a Pavel BOBÁĽ (703 Slovensko, domácí)

Vydání

RSC Advances, Cambridge, Royal Society of Chemistry, 2020, 2046-2069

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Odkaz na plný text výsledku nebo domovskou stránku výsledku.

Impakt faktor

Impact factor: 3.361

Kód RIV

RIV/00216224:14160/20:00118227

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1039/d0ra04359a

UT WoS

000545357500025

Klíčová slova anglicky

amides; cyanides; molecular oxygen

Štítky

CF PROT, rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 22. 2. 2021 12:51, Mgr. Hana Hurtová

Anotace

V originále

We have identified a novel one-pot method for the synthesis of beta-amino alcohols, which is based on C-H bond hydroxylation at the benzylic alpha-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target.

Návaznosti

LM2015043, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

Citovat

OTEVŘEL, Jan, David ŠVESTKA a Pavel BOBÁĽ. One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles. RSC Advances. Cambridge: Royal Society of Chemistry, 2020, roč. 10, č. 42, s. 25029-25045. ISSN 2046-2069. Dostupné z: https://dx.doi.org/10.1039/d0ra04359a.

@article{1744984,
   author = {Otevřel, Jan and Švestka, David and Bobáľ, Pavel},
   article_location = {Cambridge},
   article_number = {42},
   doi = {http://dx.doi.org/10.1039/d0ra04359a},
   keywords = {amides; cyanides; molecular oxygen},
   language = {eng},
   issn = {2046-2069},
   journal = {RSC Advances},
   title = {One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles},
   url = {https://pubs.rsc.org/en/content/articlepdf/2020/ra/d0ra04359a},
   volume = {10},
   year = {2020}
}

TY  - JOUR
ID  - 1744984
AU  - Otevřel, Jan - Švestka, David - Bobáľ, Pavel
PY  - 2020
TI  - One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
JF  - RSC Advances
VL  - 10
IS  - 42
SP  - 25029-25045
EP  - 25029-25045
PB  - Royal Society of Chemistry
SN  - 20462069
KW  - amides
KW  - cyanides
KW  - molecular oxygen
UR  - https://pubs.rsc.org/en/content/articlepdf/2020/ra/d0ra04359a
N2  - We have identified a novel one-pot method for the synthesis of beta-amino alcohols, which is based on C-H bond hydroxylation at the benzylic alpha-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target.
ER  -

OTEVŘEL, Jan, David ŠVESTKA a Pavel BOBÁĽ. One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles. \textit{RSC Advances}. Cambridge: Royal Society of Chemistry, 2020, roč.~10, č.~42, s.~25029-25045. ISSN~2046-2069. Dostupné z: https://dx.doi.org/10.1039/d0ra04359a.

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