Abstract
It was shown that arylbromides bearing electron-withdrawing groups in appropriate positions can be subjected to Sonogashira coupling with terminal alkynes, producing internal alkynes that can now undergo a Michael addition with suitable secondary amines. This coupling-aminovinylation sequence can be performed in a one-pot fashion, providing a straightforward access to push-pull chromophores. By applying acid chlorides instead of arylbromides, it was possible to synthesize ynones that are highly reactive and valuable intermediates. Furthermore, we succeeded in directly converting these building blocks into beta-enaminones, pyrimidines and halofurans in a one-pot three-component fashion.
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