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Zirconium‐Mediated Multicomponent Reactions of 1,3‐Butadiynes with Ylidenemalononitriles to Form Functionalized 1,8‐Naphthyridine and Cyclopenta[ b ]pyridine Derivatives
Author(s) -
Yu Shasha,
Sun Renhong,
Chen Haoyi,
Xie Xin,
Liu Yuanhong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405899
Subject(s) - transmetalation , chemistry , pyridine , yield (engineering) , stereoselectivity , zirconium , medicinal chemistry , molecule , domino , stereochemistry , organic chemistry , materials science , catalysis , metallurgy
Zirconocene‐mediated multicomponent reactions of 1,3‐butadiynes with ylidenemalononitriles in the absence or presence of CuCl have been developed. In the absence of CuCl, 1,3‐butadiyne couples with three molecules of ylidenemalononitriles to yield azazirconacycles bearing a hexahydro‐1,8‐naphthyridine skeleton with high stereoselectivity. In the presence of CuCl, cyclopenta[ b ]pyridine or cyclopenta[ b ]quinolin‐1‐one derivatives are obtained via transmetalation of ZrC bond to CuC bond as the key reaction step. These domino‐type reactions proceed with high chemo‐, regio‐ and/or stereoselectivities, and allowing the formation of multiple CN and CC bonds in a single operation.