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@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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