148290-50-0Relevant academic research and scientific papers
Aryl Radical Additions to Aldehydes and Oxime Ethers: The Tandem Enediyne-Radical Cyclization
Grissom, Janet Wisniewski,Klingberg, Detlef
, p. 6559 - 6564 (1993)
The previously unreported cyclization of aryl radicals onto aldehyde and oxime ether acceptors is described.The aryl radicals were generated from a cyclization of enediyne substrates.The aldehydes 6 and 9 and the oxime ethers 7 and 10 were heated to 190 deg C in chlorobenzene in the presence of 1,4-cyclohexadiene as a hydrogen atom source to yield the tandem enediyne-radical cyclization products 11a, 11b, 14, 21, and 22, and the simple enediyne cyclization products 12, 13, 15, 16, and 23.For the enediyne aldehyde substrates tandem enediyne-radical cyclization does not appear to be a synthetically useful process and a mixture of products was obtained.The aryl radicals generated in these enediyne cyclizatios subsequently undergo either a radical cyclization or other reactions such as hydrogen abstraction from 1,4-cyclohexadiene, decarbonylation, or intramolecular 1,5- and 1,6-hydrogen abstractinos.In contrast, the reactions with oxime ether precursors provide the tandem enediyne-radical cyclization products in good yield and provide a useful alternative to the tandem enediyne-6-exo-radical cyclization onto olefins.
Novel acyclic enediynes inhibit Cyclin A and Cdc25C expression and induce apoptosis phenomenon to show potent antitumor proliferation
Lo, Yu-Hsiang,Lin, I-Ling,Lin, Chi-Fong,Hsu, Cheng-Chung,Yang, Sheng-Huei,Lin, Shinne-Ren,Wu, Ming-Jung
, p. 4528 - 4536 (2007)
A series of acyclic enediynes showing significant inhibition on the growth of tumor cancer is disclosed. To investigate the structure-activity relationship, compounds 12-33 were synthesized. Among them, compound 17 showed most potent growth inhibition act
Experimental and computational evidence for gold vinylidenes: Generation from terminal alkynes via a bifurcation pathway and facile C-H insertions
Ye, Longwu,Wang, Yanzhao,Aue, Donald H.,Zhang, Liming
supporting information; experimental part, p. 31 - 34 (2012/02/15)
Facile cycloisomerization of (2-ethynylphenyl)alkynes is proposed to be promoted synergistically by two molecules of BrettPhosAuNTf2, affording tricyclic indenes in mostly good yields. A gold vinylidene is most likely generated as one of the reaction intermediates on the basis of both mechanistic studies and theoretical calculations. Different from the well-known Rh, Ru, and W counterparts, this novel gold species is highly reactive and undergoes facile intramolecular C(sp3)-H insertions as well as O-H and N-H insertions. The formation step for the gold vinylidene is predicted theoretically to be complex with a bifurcated reaction pathway. A pyridine N-oxide acts as a weak base to facilitate the formation of an alkynylgold intermediate, and the bulky BrettPhos ligand in the gold catalyst likely plays a role in sterically steering the reaction toward formation of the gold vinylidene.
CDPI3-Enediyne and CDPI3-EDTA Conjugates: A New Class of DNA Cleaving Agents
Boger, Dale L.,Zhou, Jiacheng
, p. 3018 - 3024 (2007/10/02)
The synthesis and preliminary evaluation of 1a and 1b, prototypical CDPI3-enediyne and CDPI3-EDTA conjugates constituting a new class of DNA cleaving agents, are detailed.
Synthetic studies of the tandem enediyne-mono- and bis-radical cyclizations
Grissom, Janet Wisniewski,Calkins, Trevor L.,Egan, Miles
, p. 11744 - 11752 (2007/10/02)
The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dihydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to i
