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 and Pavel BOBÁĽ

Basic information

Original name

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

Authors

OTEVŘEL, Jan (203 Czech Republic, guarantor, belonging to the institution), David ŠVESTKA (203 Czech Republic, belonging to the institution) and Pavel BOBÁĽ (703 Slovakia, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Odkaz na plný text výsledku nebo domovskou stránku výsledku.

Impact factor

Impact factor: 3.361

RIV identification code

RIV/00216224:14160/20:00118227

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

000545357500025

Keywords in English

amides; cyanides; molecular oxygen

Abstract

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.

Links

LM2015043, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

OTEVŘEL, Jan, David ŠVESTKA and 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, vol. 10, No 42, p. 25029-25045. ISSN 2046-2069. Available from: 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 and 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, vol.~10, No~42, p.~25029-25045. ISSN~2046-2069. Available from: https://dx.doi.org/10.1039/d0ra04359a.

Detailed Information on Publication Record