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Synthesis of imines

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Schmidt Reaction


Schmidt Reaction


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Neat non-volatile amines react efficiently with various aromatic aldehydes in the absence of any catalyst or solvent, to give imines after a reaction time of eight minutes under microwave irradiation. 1,3-dimethylurea dispersed on montmorillonite K10 is used as an methylamine precursor.
L. Paquin, J. Hamelin, F. Texier-Boullet, Synthesis, 2006, 1635-1638.


Manganese dioxide is employed as an in situ oxidant for the one-pot conversion of alcohols into imines. In combination with polymer-supported cyanoborohydride (PSCBH), a one-pot oxidation-imine formation-reduction sequence enables alcohols to be converted directly into both secondary and tertiary amines.
L. Blackburn, R. J. K. Taylor, Org. Lett., 2001, 3, 1637-1639.


A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and 3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such as piperazine, morpholine, and 1,4-diazepane annulated β-lactam derivatives.
W. Van Brabandt, M. Vanwalleghem, M. D'hooghe, N. De Kimpe, J. Org. Chem., 2006, 71, 7083-7086.


Readily available and stable titanocene-alkyne complexes can be used for the hydroamination of internal and terminal alkynes. The reactions of terminal alkynes with aliphatic amines proceed highly selectively to give the corresponding primary anti-Markovnikov functionalized imines in good to excellent yields.
A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. Int. Ed., 2002, 41, 2541-2543.


A number of new reactions of IBX with heteroatom-containing substrates were discovered and their utility was demonstrated. IBX was used for the generation of imines from secondary amines in notably high yields, for the oxidative aromatization of nitrogen heterocycles and for the cleavage of dithianes.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem., 2003, 115, 4211-4216.


[RuCl2(CO)3]2/dppp is a highly effective catalyst system for the intramolecular oxidative amination of various aminoalkenes in presence of K2CO3 and allyl acetate in N-methylpiperidine to give the corresponding cyclic imines and indoles in excellent yields.
T. Kondo, T. Okada, T.-A. Mitsudo, J. Am. Chem. Soc., 2002, 124, 186-187.