Tetrahedron

Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 1: The search for alkenyl-DPPs. Unsaturated nitriles in standard DPP syntheses: a novel …

…, DM Smith, P Lightfoot, AMZ Slawin, EJ MacLean

文献索引：Morton, Colin J.H; Gilmour, Ryan; Smith, David M; Lightfoot, Philip; Slawin, Alexandra M.Z; MacLean, Elizabeth J Tetrahedron, 2002 , vol. 58, # 27 p. 5547 - 5565

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被引用次数: 53

摘要

Reactions of the anion of ethyl 4, 5-dihydro-5-oxo-2-phenylpyrrole-3-carboxylate with the Diels–Alder adducts of acrylonitrile and various dienes rarely yield the expected DPP derivatives. The reaction with cyclohex-3-enecarbonitrile provides a noteworthy exception: thermolysis of the resulting cyclohexenyl-DPP gives butadiene and impure 3-ethenyl-6- phenyl-DPP, the latter being thermally unstable. Michael additions predominate when the ...