54879-83-3Relevant 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.
Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis
Ioanoviciu, Alexandra,Antony, Smitha,Pommier, Yves,Staker, Bart L.,Stewart, Lance,Cushman, Mark
, p. 4803 - 4814 (2007/10/03)
Several norindenoisoquinolines substituted with methoxy or methylenedioxy groups have been prepared and their anticancer properties evaluated in cancer cell cultures and in topoisomerase I inhibition assays. 2,3-Dimethoxy-8,9- methylenedioxy-11H-indeno[1,
Studies Directed Towards Total Syntheses of the Tropoloisoquinoline Alkaloids Grandirubrine and Imerubrine. I. Preparation of Two 4,5,6-Trimethoxycyclopentisoquinolin-7-ones and Their Response to Robinson Annulation Conditions
Banwell, Martin G.,Bonadio, Anna,Turner, Kathleen A.,Ireland, Neil K.,Mackay, Maureen F.
, p. 325 - 351 (2007/10/02)
In connection with efforts to develop total syntheses of the tropoloisoquinoline alkaloids grandirubrine (1) and imerubrine (2), preparations of tricyclic ketone (8) and the related ethoxycarbonyl system (47) are described.Of the various approaches to (8)