405198-85-8Relevant academic research and scientific papers
“Golden” Cascade Cyclization to Benzo[c]-Phenanthridines
Hendrich, Christoph M.,Senn, Sebastian,Haas, Lea,Hoffmann, Marvin T.,Zschieschang, Ute,Greiner, Luca C.,Rominger, Frank,Rudolph, Matthias,Klauk, Hagen,Dreuw, Andreas,Hashmi, A. Stephen K.
supporting information, p. 14778 - 14784 (2021/09/14)
Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6-endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Boc-protected dihydrobenzo[c]phenanthridines with yields of up to 98 %; even a π-extension and two bidirectional approaches were successful. Furthermore, thermal cleavage of the Boc group and subsequent oxidation gave substituted benzo[c]phenanthridines in up to quantitative yields. Two bidirectional approaches under the optimized conditions were successful, and the resulting π-extended molecules were tested as organic semiconductors in organic thin-film transistors.
Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions
Aronica, Laura Antonella,Albano, Gianluigi,Giannotti, Luca,Meucci, Elisa
supporting information, p. 955 - 963 (2017/02/15)
A protocol based on cyclocarbonylative Sonogashira reactions has been developed for the synthesis of nitrogen-containing heterocycles. The process is carried out under CO pressure, in the presence of a small amount of PdCl2(PPh3)sub
Chemistry and folding of photomodulable peptides - Stilbene and thioaurone-type candidates for conformational switches
Erdelyi, Mate,Varedian, Miranda,Skoeld, Christian,Niklasson, Ida B.,Nurbo, Johanna,Persson, Asa,Bergquist, Jonas,Gogoll, Adolf
experimental part, p. 4356 - 4373 (2009/02/07)
Optimized synthetic strategies for the preparation of photoswitchable molecular scaffolds based on stilbene or on thioaurone chromophores and their conformationally directing properties, as studied by computations and by NMR spectroscopy, are addressed. For the stilbene peptidomimetics 1, 2 and 3, the length of connecting linkers between the chromophore and the peptide strands was varied, resulting in photochromic dipeptidomimetics with various flexibility. Building blocks of higher rigidity, based on para-substituted thioaurone (4 and 6) and meta-substituted thioaurone chromophores (5 and 7) are shown to have a stronger conformationally directing effect. Design, synthesis, theoretical and experimental conformational analyses are presented.
Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride
Hiroya, Kou,Jouka, Rumi,Kameda, Mitsuyoshi,Yasuhara, Akito,Sakamoto, Takao
, p. 9697 - 9710 (2007/10/03)
The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested.
