- Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines
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Ring-closing olefin metathesis (RCM) has been applied to the efficient synthesis of densely and diversely substituted pyridine and pyridazine frameworks. Routes to suitable metathesis precursors have been investigated and the scope of the metathesis step has been probed. The metathesis products function as precursors to the target heteroaromatic structures via elimination of a suitable leaving group, which also facilitates earlier steps by serving as a protecting group at nitrogen. Further functionalisation of the metathesis products is possible both prior to and after aromatisation. The net result is a powerful strategy for the de novo synthesis of highly substituted heteroaromatic scaffolds.
- Donohoe, Timothy J.,Bower, John F.,Basutto, José A.,Fishlock, Lisa P.,Procopiou, Panayiotis A.,Callens, Cedric K.A.
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scheme or table
p. 8969 - 8980
(2009/12/26)
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- Synthesis of substituted pyridines and pyridazines via ring closing metathesis
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RCM can be used to make aromatic heterocycles, namely pyridines and, for the first time, pyridazines; the key step after RCM involves elimination of sulfinate to provide the aromatic system. The Royal Society of Chemistry 2009.
- Donohoe, Timothy J.,Fishlock, Lisa P.,Basutto, Jose A.,Bower, John F.,Procopiou, Panayiotis A.,Thompson, Amber L.
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supporting information; experimental part
p. 3008 - 3010
(2009/12/01)
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- Synthesis of 3-hydroxypyridines using ruthenium-catalyzed ring-closing olefin metathesis
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(Chemical Equation Presented) New synthetic routes to substituted 3-hydroxypyridines 6 are presented. Ring-closing olefin metathesis (RCM)/elimination and RCM/oxidation/ deprotection of nitrogen-containing dienes 4 are the key processes of the routes. An
- Yoshida, Kazuhiro,Kawagoe, Fumihiro,Hayashi, Kazushi,Horiuchi, Shingo,Imamoto, Tsuneo,Yanagisawa, Akira
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supporting information; experimental part
p. 515 - 518
(2009/07/10)
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- 2-formylpyridine thiosemicarbazone compounds
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A method of treatment of tumors is provided based upon a compound of the formula STR1 Some aspects of the invention were supported in part by U.S. Public Health Service Grant CA-02817 from the National Cancer Institute and support from the Northeast NMR Facility at Yale University insofar as the use of high resolution NMR spectra is concerned that was made possible by a grant from the Chemical Division of the National Science Foundation (Grant No. CHE-7916210).
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- Synthesis and Antitumor Activity of 3- and 5-Hydroxy-4-methylpyridibe-2-carboxaldehyde Thiosemicarbazones
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To develop an α-(N)-heterocyclic carboxaldehyde thiosemicarbazone with clinical utility as an anticancer agent, two analogues, 3-hydroxy-4-methylpyridine-2-carboxaldehyde thiosemicarbazone (3-HMP) and 5-hydroxy-4-methylpyridine-2-carboxaldehyde thiosemicarbazone (5-HMP), of 5-hydroxypyridine-2-carboxaldehyde thiosemicarbazone (5-HP) have been designed and synthesized by two different methods. 3-HMP and 5-HMP both showed better antitumor activity than their respective parent compounds, 3-hydroxypyridine-2-carboxaldehyde thiosemicarbazone and 5-HP, in mice bearing the L1210 leukemia.
- Wang, Yuqiang,Liu, Mao-Chin,Lin, Tai-Shun,Sartorelli, Alan C.
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p. 3667 - 3671
(2007/10/02)
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