C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14160%2F24%3A00136114" target="_blank" >RIV/00216224:14160/24:00136114 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2024/ra/d3ra08974f" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2024/ra/d3ra08974f</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d3ra08974f" target="_blank" >10.1039/d3ra08974f</a>
Alternative languages
Result language
angličtina
Original language name
C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10400 - Chemical sciences
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
RSC Advances
ISSN
2046-2069
e-ISSN
2046-2069
Volume of the periodical
14
Issue of the periodical within the volume
24
Country of publishing house
GB - UNITED KINGDOM
Number of pages
17
Pages from-to
16784-16800
UT code for WoS article
001230633000001
EID of the result in the Scopus database
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