- Structure and Mechanism Revision of a Catalyzed Cyclization of Benzaldehyde Bearing Alkyne-Nitrile
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Pt(II)-catalyzed carbocyclization of benzaldehyde containing a keto-nitrile functionality resulted in the formation, respectively, of isochromenes and spiro-lactones instead of fused lactams and spiro-lactams as was previously reported. The reaction mecha
- ?afá?, Peter,Marchalín, ?tefan,?oral, Michal,Moncol, Ján,Da?ch, Adam
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- Chemoselectivities in the platinum-catalyzed hydrative carbocyclizations of oxo-alkyne-nitrile functionalities
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Two new hydrative carbocyclizations of oxa-alkyne-nitrile functionalities are reported to produce distinct nitrogen-containing heterocycles. Protracted heating of oxoalkynyl nitrile substrates with PtCl2/CO/H2O in hot 1,4-dioxane gave 2,3-dihydro-1H-pyrido[1.2-b]-isoquinolin-4(6H)-ones. In this hydration reaction, dicarbonyl nitrile intermediates were isolated efficiently after a brief period, and they were subjected to an NHC-based crossed benzoin coupling to give spiro alcohols that further reacted with TfOH to give spiro[indene-2,2′-piperidine]-1,6′(3H)-diones.
- Mukherjee, Anupam,Liu, Rai-Shung
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supporting information; experimental part
p. 660 - 663
(2011/05/03)
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