A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes

  title={A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes},
  author={Hiromichi Fujioka and Kenichi Murai and Yusuke Ohba and Atsushi Hiramatsu and Yasuyuki Kita},
  journal={Tetrahedron Letters},
Abstract The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0 °C–rt to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitriles, and esters can exist. 
74 Citations
A Mild and Efficient One‐Pot Synthesis of 2‐Dihydroimidazoles from Aldehydes.
Abstract The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0 °C–rt to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and manyExpand
Efficient, Rapid and One Pot Synthesis of 2-substituted Benzimidazoles Using the NaOH/I2 System as an Oxidant Under Mild Conditions
A one-pot efficient synthesis of benzimidazole derivatives has been achieved from aryl aldehydes and o-phenylenediamine in the presence of the NaOH/I2 system at room temperature in acetonitrile. TheExpand
One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates
Abstract Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphaticExpand
[Development and application of practical synthetic methods of imidazolines].
  • Kenichi Murai
  • Chemistry, Medicine
  • Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
  • 2010
The first method to prepare imidazolines from aldehydes and 1,2-diamines by condensation and successive oxidation using NBS in one-pot operation is described. Expand
An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water
Abstract The system, I 2 /KI/K 2 CO 3 /H 2 O, oxidizes carbon–nitrogen bonds for the synthesis of imidazolines and benzimidazoles from aldehydes and diamines under anaerobic conditions in water at 90Expand
An efficient synthesis of 2-arylimidazoles by oxidation of 2-arylimidazolines using activated carbon–O2 system and its application to palladium-catalyzed Mizoroki–Heck reaction
Abstract Oxidative conversion of 2-substituted imidazoline (dihydroimidazole) to the corresponding imidazole was achieved by an activated carbon–O2 system. Also, the 2-arylimidazolines andExpand
Oxidative decarboxylative synthesis of 2-H-imidazolines from glyoxylic acid and 1,2-diamines.
A novel method to prepare 2-H-imidazolines from glyoxylic acid monohydrate and 1,2-diamines is described; the key reaction of this method is the oxidative decarboxylation of the 2-carboxyExpand
Environment-friendly and solvent-free synthesis of symmetrical bis-imines under microwave irradiation
Abstract A short library of symmetrical bis-imines has been constructed efficiently from the reaction between dialdehydes and mono amines or diamines and mono aldehydes under microwave irradiationExpand
Microwave-enhanced synthesis of cyclic amidines
Abstract We present a simple and efficient microwave based protocol for the synthesis of heterocyclic amidines by PPE promoted cyclodehydration of N -aryl- N ′-acylalkylenediamines. The method isExpand
Efficient Synthesis of 2-Imidazolines in the Presence of Molecular Iodine Under Ultrasound Irradiation
An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25–30°C under ultrasoundExpand


A novel synthetic method for 2-arylmethyl substituted imidazolines and imidazoles from 2-aryl-1,1-dibromoethenes
Abstract Various 2-arylmethylimidazolines were prepared by treating readily available 2-aryl-1,1-dibromoethenes with ethylenediamine under mild conditions and further converted into the correspondingExpand
An efficient method for the preparation of N,N-disubstituted 1,2-diamines
C2-Symmetric 1,2-diamines are useful precursors to numerous reagents used in asymmetric synthesis and catalysis. We report here an efficient protocol for converting the two most commonly usedExpand
Use of optically active cyclic N,N-dialkyl aminals in asymmetric induction.
[reaction: see text]Cyclization of the optically active ketone N,N-dialkyl aminals A affords the diastereomer B as the major product with diastereoselectivities ranging from nearly 1:1 to essentiallyExpand
A new route to homochiral piperidines
Abstract The synthesis of an enantiomeric pair of enaminoesters from phenylglycine is described. Conjugate addition to α,β-enones, reductive cyclization-fragmentation to octahydroimidazopyridines andExpand
Synthesis and application of chiral phosphino-imidazoline ligands: Ir-catalyzed enantioselective hydrogenation.
[reaction: see text] A series of chiral phosphino-imidazolines (PHIM ligands) 1a-j with different substituents at the stereogenic center, the nitrogen atom of the imidazoline ring, and at theExpand
Stereoselective Synthesis of Quaternary Benzylic Carbons Using C2 Symmetric Imidazolines and Tetrahydrofuran as Electrophile
Alkylative ring opening of tetrahydrofuran in the presence of 9-BBN triflate is studied. Dianions derived from C2 symmetric imidazolines induce excellent to modest acyclic diastereoselectivity toExpand
Thiamine coenzyme models: Imidazolinium ylides and the reactions of 2-(hydroxyalkyl)imidazolines
Abstract Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-2-imidazolines (adducts of the aldehydes with 1-benzyl-2-1ithio-2-imidazoline) whereasExpand
Chiral pyridylimidazolines: synthesis, arene ruthenium complexes and application in asymmetric catalysis
Condensation of (1S,2S)-1,2-diphenylethylenediamine and 2-cyanopyridine gives the chiral pyridylimidazoline (L1), deprotonation followed by treatment with methyl iodide gives an NMe derivative (L2).Expand
Highly efficient enantiospecific synthesis of imidazoline-containing amino acids using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate.
A highly efficient enantiospecific synthesis of imidazoline-based amino acids is reported from dipeptides composed of a C-terminal beta-amino-alpha-amino acid residue using bis(triphenyl)Expand
Asymmetrische katalysen: XLVI. Enantioselektive Hydrosilylierung von Ketonen mit [Rh(COD)Cl]2 und optisch aktiven Stickstoff-Liganden
The synthesis and characterisation of 16 optically active nitrogen ligands, namely, pyridinethiazolidones, pyridinethiazolines, pyridinimidazolines, Schiff bases and bipyridines, are described. TheseExpand