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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 a Zoltan MUCSI. C(sp3)-H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines. \textit{RSC Advances}. Cambridge: Royal Society of Chemistry, 2024, roč.~14, č.~24, s.~16784-16800. ISSN~2046-2069. Dostupné z: https://dx.doi.org/10.1039/d3ra08974f.
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