- Copper-catalyzed cross-coupling of O -alkyl hydroxamates with aryl iodides
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N-Aryl-O-alkylhydroxamic acid derivatives were prepared by copper-catalyzed cross-coupling of hydroxamates with aryl iodides. The reaction conditions are compatible with standard hydroxy-protecting groups on the hydroxylamine moiety and are applicable to
- Kukosha, Tatyana,Trufilkina, Nadezhda,Belyakov, Sergey,Katkevics, Martins
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supporting information; experimental part
p. 2413 - 2423
(2012/09/07)
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- Synthesis of N-alkoxyindol-2-ones by copper-catalyzed intramolecular N-arylation of hydroxamates
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The first example of copper-catalyzed intramolecular N-arylation of hydroxamic acid derivatives is presented. Based on this transformation a new method for the synthesis of N-alkoxyindol-2-ones from 2-(2-bromoaryl) acetylhydroxamates has been developed. T
- Kukosha, Tatyana,Trufilkina, Nadezhda,Katkevics, Martins
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supporting information; experimental part
p. 2525 - 2528
(2011/11/13)
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- Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group
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N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.
- Kawase, Masami,Kitamura, Takahiro,Kikugawa, Yasuo
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p. 3394 - 3403
(2007/10/02)
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