53366-27-1Relevant articles and documents
Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization
Ji, Xiang,Huang, Zheng,Lumb, Jean-Philip
, p. 1062 - 1072 (2020/01/31)
Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQ) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products.
Potent and selective xanthine-based inhibitors of phosphodiesterase 5
Arnold, Nichola J.,Arnold, Ruth,Beer, David,Bhalay, Gurdip,Collingwood, Stephen P.,Craig, Sarah,Devereux, Nicholas,Dodds, Mark,Dunstan, Andrew R.,Fairhurst, Robin A.,Farr, David,Fullerton, Joseph D.,Glen, Angela,Gomez, Sylvie,Haberthuer, Sandra,Hatto, Julia D.I.,Howes, Colin,Jones, Darryl,Keller, Thomas H.,Leuenberger, Beate,Moser, Heinz E.,Muller, Irene,Naef, Reto,Nicklin, Paul A.,Sandham, David A.,Turner, Katharine L.,Tweed, Morris F.,Watson, Simon J.,Zurini, Mauro
, p. 2376 - 2379 (2007/10/03)
Inhibitors of PDE5 are useful therapeutic agents for treatment of erectile dysfunction. A series of novel xanthine derivatives has been identified as potent inhibitors of PDE5, with good levels of selectivity against other PDE isoforms, including PDE6. St
Regioselectivity in the Synthesis of Isoquinolines with Methoxy Activating Groups
Euerby, Melvin R.,Waigh, Roger D.
, p. 501 - 526 (2007/10/02)
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