C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines

J 2024

C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines

DUNKEL, Petra, Dora BOGDÁN, Ruth DEME, Adam ZIMBER, Veronika BALLAYOVÁ et. al.

Basic information

Original name

C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines

Authors

DUNKEL, Petra, Dora BOGDÁN (348 Hungary), Ruth DEME (348 Hungary), Adam ZIMBER (348 Hungary), Veronika BALLAYOVÁ (703 Slovakia, belonging to the institution), Eszter CSIZMADIA (348 Hungary), Bence KONTRA, Eszter KALYDI (348 Hungary), Attila BENYEI (348 Hungary), Peter MATYUS (348 Hungary) and Zoltan MUCSI (348 Hungary)

Edition

RSC Advances, Cambridge, Royal Society of Chemistry, 2024, 2046-2069

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.900 in 2022

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.1039/d3ra08974f

UT WoS

001230633000001

Keywords in English

H BOND FUNCTIONALIZATION; RING CLOSURE REACTIONS; HETEROCYCLIC SYNTHESIS; STEREOCHEMICAL ASPECTS; ASYMMETRIC SYNTHESIS; TANDEM; PYRROLO<1 2 A> QUINOLINES; TRANSFER/CYCLIZATION; TETRAHYDROQUINOLINES; CONSTRUCTION

Abstract

V originále

1,5-hydride transfer-triggered cyclization reactions offering a robust method for C(sp(3))-C(sp(3)) coupling and the synthesis of e.g. tetrahydroquinolines have been thoroughly investigated in the literature. Catalysts allowing milder reaction conditions or the development of enantioselective processes were important recent contributions to the field, as well as the studies on subtrates with oxygen or sulfur heteroatoms (besides the originally described nitrogen heterocycles). In a series of studies, we focused on expanded, higher order H-transfers/cyclizations by positioning the interacting substituents on distanced rings. Cyclizations of appropriately functionalized biaryl and fused bicyclic systems led to 7-9 membered rings. In the frame of this research, we set out to study the feasibility of the cyclization and the factors affecting it by in silico methods. The conclusions drawn from computational studies were complemented by cyclization screens on 2-(2-vinyl)phenoxy-tert-anilines and their CH2-expanded analogues, the results of which are presented here. Besides isolating the expected oxazonine products in several cases, we also observed a unique dimer formation, leading to an interesting 5-6-5 ring system.

Citovat

DUNKEL, Petra, Dora BOGDÁN, Ruth DEME, Adam ZIMBER, Veronika BALLAYOVÁ, Eszter CSIZMADIA, Bence KONTRA, Eszter KALYDI, Attila BENYEI, Peter MATYUS and Zoltan MUCSI. C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines. RSC Advances. Cambridge: Royal Society of Chemistry, 2024, vol. 14, No 24, p. 16784-16800. ISSN 2046-2069. Available from: https://dx.doi.org/10.1039/d3ra08974f.

@article{2407758,
   author = {Dunkel, Petra and Bogdán, Dora and Deme, Ruth and Zimber, Adam and Ballayová, Veronika and Csizmadia, Eszter and Kontra, Bence and Kalydi, Eszter and Benyei, Attila and Matyus, Peter and Mucsi, Zoltan},
   article_location = {Cambridge},
   article_number = {24},
   doi = {http://dx.doi.org/10.1039/d3ra08974f},
   keywords = {H BOND FUNCTIONALIZATION; RING CLOSURE REACTIONS; HETEROCYCLIC SYNTHESIS; STEREOCHEMICAL ASPECTS; ASYMMETRIC SYNTHESIS; TANDEM; PYRROLO<1 2 A> QUINOLINES; TRANSFER/CYCLIZATION; TETRAHYDROQUINOLINES; CONSTRUCTION},
   language = {eng},
   issn = {2046-2069},
   journal = {RSC Advances},
   title = {C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines},
   url = {https://pubs.rsc.org/en/content/articlelanding/2024/ra/d3ra08974f},
   volume = {14},
   year = {2024}
}

TY  - JOUR
ID  - 2407758
AU  - Dunkel, Petra - Bogdán, Dora - Deme, Ruth - Zimber, Adam - Ballayová, Veronika - Csizmadia, Eszter - Kontra, Bence - Kalydi, Eszter - Benyei, Attila - Matyus, Peter - Mucsi, Zoltan
PY  - 2024
TI  - C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines
JF  - RSC Advances
VL  - 14
IS  - 24
SP  - 16784-16800
EP  - 16784-16800
PB  - Royal Society of Chemistry
SN  - 20462069
KW  - H BOND FUNCTIONALIZATION
KW  - RING CLOSURE REACTIONS
KW  - HETEROCYCLIC SYNTHESIS
KW  - STEREOCHEMICAL ASPECTS
KW  - ASYMMETRIC SYNTHESIS
KW  - TANDEM
KW  - PYRROLO<1 2 A>
KW  - QUINOLINES
KW  - TRANSFER/CYCLIZATION
KW  - TETRAHYDROQUINOLINES
KW  - CONSTRUCTION
UR  - https://pubs.rsc.org/en/content/articlelanding/2024/ra/d3ra08974f
N2  - 1,5-hydride transfer-triggered cyclization reactions offering a robust method for C(sp(3))-C(sp(3)) coupling and the synthesis of e.g. tetrahydroquinolines have been thoroughly investigated in the literature. Catalysts allowing milder reaction conditions or the development of enantioselective processes were important recent contributions to the field, as well as the studies on subtrates with oxygen or sulfur heteroatoms (besides the originally described nitrogen heterocycles). In a series of studies, we focused on expanded, higher order H-transfers/cyclizations by positioning the interacting substituents on distanced rings. Cyclizations of appropriately functionalized biaryl and fused bicyclic systems led to 7-9 membered rings. In the frame of this research, we set out to study the feasibility of the cyclization and the factors affecting it by in silico methods. The conclusions drawn from computational studies were complemented by cyclization screens on 2-(2-vinyl)phenoxy-tert-anilines and their CH2-expanded analogues, the results of which are presented here. Besides isolating the expected oxazonine products in several cases, we also observed a unique dimer formation, leading to an interesting 5-6-5 ring system.
ER  -

DUNKEL, Petra, Dora BOGDÁN, Ruth DEME, Adam ZIMBER, Veronika BALLAYOVÁ, Eszter CSIZMADIA, Bence KONTRA, Eszter KALYDI, Attila BENYEI, Peter MATYUS and Zoltan MUCSI. C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines. \textit{RSC Advances}. Cambridge: Royal Society of Chemistry, 2024, vol.~14, No~24, p.~16784-16800. ISSN~2046-2069. Available from: https://dx.doi.org/10.1039/d3ra08974f.

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