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- W2099140934 abstract "Abstract Pyridinium salts Py + ‐CH 2 ‐EWG (EWG = CO 2 Et, CONEt 2 , CN, COMe, COPh) reacted with Michael acceptors Ar‐CH=C(CO 2 Et)(Acc) (Acc = CO 2 Et, COMe, SO 2 Me, CONH 2 ) at ambient temperature in the presence of base to give [3 + 2]‐cycloadducts by stepwise [3 + 2]‐cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1‐(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc). A good yield of indolizine was also obtained from Py + ‐CH 2 CN and i Pr‐CH=C(CO 2 Et) 2 , which indicates that this method is not restricted to aromatic Michael acceptors. Structurally related isoquinolinium salts react with Michael acceptors analogously to give pyrrolo[2,1‐ a ]isoquinolines." @default.
- W2099140934 created "2016-06-24" @default.
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- W2099140934 date "2013-08-12" @default.
- W2099140934 modified "2023-10-16" @default.
- W2099140934 title "One-Pot Two-Step Synthesis of 1-(Ethoxycarbonyl)indolizines via Pyridinium Ylides" @default.
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- W2099140934 doi "https://doi.org/10.1002/ejoc.201300784" @default.
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