Rhodium( i )-catalysed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides leading to 3-(cis-alken-1-yl)-2-aminoquinolines

Rhodium( i )-catalysed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides leading to 3-(cis-alken-1-yl)-2-aminoquinolines

Cycloisomerization of N -[2-(2-alkyn-1-yl)phenyl]carbodiimides 1 catalysed by Rh(dppp) 2 Cl under heating conditions afforded 3-( cis -alken-1-yl)-2-(substituted amino)quinolines in up to 87% yield with high cis -selectivity. Scope, limitations, a proposed mechanism for these reactions, and a one-po...

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Veröffentlicht in:RSC advances 2014-01, Vol.4 (96), p.53669-53673
Hauptverfasser: Otani, Takashi, Onishi, Misato, Seino, Takafumi, Furukawa, Naoki, Saito, Takao
Format: Artikel
Sprache:eng
Schlagworte:
Heating
Isomerization
Olefins
Synthesis
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Zusammenfassung:Cycloisomerization of N -[2-(2-alkyn-1-yl)phenyl]carbodiimides 1 catalysed by Rh(dppp) 2 Cl under heating conditions afforded 3-( cis -alken-1-yl)-2-(substituted amino)quinolines in up to 87% yield with high cis -selectivity. Scope, limitations, a proposed mechanism for these reactions, and a one-pot synthesis of their trans -isomers from 1 with iodine-promoted olefin isomerization are described.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA11846D