• Title/Summary/Keyword: Allylation

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Synthesis of Dienamides via the Reaction of Nitrile with Allylindium Reagents and Intramolecular Acyl Group Quenching Cascade

  • Kim, Sung-Hwan;Kim, Yu-Mi;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2351-2356
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    • 2010
  • Various dienamide derivatives were synthesized in reasonable yields from benzonitriles having an amide moiety at the ortho-position, via the sequential (i) In-mediated allylation of nitrile moiety to form an imine intermediate, (ii) intramolecular quenching of an acyl group by the imine intermediate, and (iii) a proton transfer to dienamide.

A Facile One-Pot Operations of Reduction and Allylation of Nitrobenzaldehydes Mediated by Indium and Their Applications

  • Cho, Yong-Seo;Kang, Kyung-Ho;Cha, Joo-Hwan;Choi, Kyung-Il;Pae, Ae-Nim;Koh, Hun-Yeong;Chang, Moon-Ho
    • Bulletin of the Korean Chemical Society
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    • v.23 no.9
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    • pp.1285-1290
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    • 2002
  • Various nitrobenzaldehydes were simultaneously allylated and reduced using indium in the presence of HCl in aqueous media to give compounds having both functionality of homoallylic alcohol and aromatic amine. Sequential protection of the amino gro up and oxidation of the anilinyl homoallylic alcohol provided useful precursors of heterocyclic compounds such as dihydroindolones and dihydroquinolones, which could be efficiently synthesized through intramolecular cyclization reaction.

Zinc Mediated Barbier Type Allylation of Cyclic Imides and Subsequent Coupling Reactions with Carbon Nucleophiles

  • Kang, Seok-Won;Heo, Eun-Young;Jun, Jong-Gab;Kim, Sung-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1924-1928
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    • 2004
  • Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of $PbBr_2$. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.