Silver-Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α-Aminoalkylation of N-Arylacrylamides with Amino Acid Derivatives

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Abstract

α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.

Original languageEnglish
Pages (from-to)496-499
Number of pages4
JournalChemistry - An Asian Journal
Volume13
Issue number5
DOIs
Publication statusPublished - 2018 Mar 2

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Silver
Derivatives
Amino Acids
Cyclization
Catalysis
oxindole

Keywords

  • amino acids
  • aminoalkylation
  • C−H activation
  • oxindoles
  • pyrroloindolines
  • silver

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Silver-Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α-Aminoalkylation of N-Arylacrylamides with Amino Acid Derivatives",
abstract = "α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.",
keywords = "amino acids, aminoalkylation, C−H activation, oxindoles, pyrroloindolines, silver",
author = "Kanyiva, {Stephen Kyalo} and Sohei Makino and Takanori Shibata",
year = "2018",
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doi = "10.1002/asia.201701739",
language = "English",
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T1 - Silver-Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α-Aminoalkylation of N-Arylacrylamides with Amino Acid Derivatives

AU - Kanyiva, Stephen Kyalo

AU - Makino, Sohei

AU - Shibata, Takanori

PY - 2018/3/2

Y1 - 2018/3/2

N2 - α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.

AB - α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.

KW - amino acids

KW - aminoalkylation

KW - C−H activation

KW - oxindoles

KW - pyrroloindolines

KW - silver

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