کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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42279 | 45918 | 2009 | 8 صفحه PDF | دانلود رایگان |
A selective one-pot synthesis of carbonyl-containing N-heterocyclic compounds has been developed using a carbonylative Sonogashira/cyclisation sequence. Various catalytic protocols were studied (CO pressure, temperature, catalyst identity, base and substrate/catalyst ratio) with the objective of obtaining selectively either indoxyl or 4-quinolone products. The origin of the selectivity toward the 5- or 6-membered ring compounds was explained through the respective role of the various catalytic species involved, whether they are organic or metallic. The non-cyclic common intermediate was selectively prepared using [PdCl2(dppp)] as catalyst. By using a two-step multi-catalysis, i.e. {[Pd]+HNEt2}, 4-quinolones were obtained whereas with a tandem catalysis, i.e. {[Pd]/PR3}, indoxyls were synthesised.
A selective one-pot synthesis of carbonyl-containing N-heterocycles has been developed using a carbonylative Sonogashira/cyclisation sequence. The origin of the selectivity toward the 5- or 6-membered ring compounds was explained through the respective role of the palladium and amine or phosphine catalytic species involved.Figure optionsDownload as PowerPoint slide
Journal: Applied Catalysis A: General - Volume 369, Issues 1–2, 15 November 2009, Pages 125–132