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One-Pot Three-Component Synthesis of α-Iminonitriles by IBX/TBAB-Mediated Oxidative Strecker Reaction

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Patrice Fontaine, Angèle Chiaroni, Géraldine Masson,* and Jieping Zhu*;

Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France

Org. Lett., 2008, 10 (8), pp 1509–1512

DOI: 10.1021/ol800199b

Publication Date (Web): March 18, 2008

Section:

General Organic Chemistry

Abstract

The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded α-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of α-iminonitrile.

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Citing Articles

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
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The Journal of Organic Chemistry2011 76 (23), 9593-9601
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  The Journal of Organic Chemistry2011 76 (23), 9593-9601
  The methyl groups in TetMe-IBX lower the activation energy corresponding to the rate-determining hypervalent twisting (theoretical calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Organoiodine(V) Reagents in Organic Synthesis
Viktor V. Zhdankin
The Journal of Organic Chemistry2011 76 (5), 1185-1197
- Organoiodine(V) Reagents in Organic Synthesis
  Viktor V. Zhdankin
  The Journal of Organic Chemistry2011 76 (5), 1185-1197
  Organohypervalent iodine reagents have attracted significant recent interest as versatile and environmentally benign oxidants with numerous applications in organic synthesis. This Perspective summarizes synthetic applications of hypervalent iodine(V) ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural Characterizations, and Oxidation Reactivities in Common Organic Solvents
Jarugu Narasimha Moorthy, Kalyan Senapati, and Keshaba Nanda Parida
The Journal of Organic Chemistry2010 75 (24), 8416-8421
- 6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural Characterizations, and Oxidation Reactivities in Common Organic Solvents
  Jarugu Narasimha Moorthy, Kalyan Senapati, and Keshaba Nanda Parida
  The Journal of Organic Chemistry2010 75 (24), 8416-8421
  We designed and synthesized λ5-cyclic periodinanes 1 and 2, which are homologous to IBX (1-hydroxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) by one carbon, to thwart close packing of molecules in the crystal lattice to permit solubility in common organic ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U
Joseph D. Panarese and Stephen P. Waters
Organic Letters2010 12 (18), 4086-4089
- Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U
  Joseph D. Panarese and Stephen P. Waters
  Organic Letters2010 12 (18), 4086-4089
  2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-β-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α-Ketoamides
Marinus Bouma, Géraldine Masson and Jieping Zhu
The Journal of Organic Chemistry2010 75 (8), 2748-2751
- Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α-Ketoamides
  Marinus Bouma, Géraldine Masson and Jieping Zhu
  The Journal of Organic Chemistry2010 75 (8), 2748-2751
  Reaction of aromatic aldehydes and isocyanides in the presence of N-methylhydroxyamine, acetic acid, and zinc chloride affords the aryl α-ketoamides in moderate to good yields.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links