Categories: Synthesis of N-Heterocycles >
Synthesis of 2,3-dihydro-4-pyridones
The aza Diels-Alder reaction of an in situ generated novel iododiene works well with aryl- and benzyl-N-substituted imines. Moderate diastereoselectivities can be obtained using simple α-methylbenzyl chiral imines.
C. Timmons, A. Kattuboina, L. McPherson, J. Mills, G. Li, Tetrahedron, 2005, 61, 11837-11842.
A reaction between N-benzylideneanilines and Danishefsky's diene proceeds smoothly in acidic aqueous medium in the presence of a catalytic amount of copper(II) triflate and sodium dodecyl sulfate to afford the corresponding 1,2-diphenyl-2,3-dihydro-4-pyridones in excellent yields. The aqueous solution containing the catalyst can be recovered and reused without any loss in efficiency.
D. Lanari, O. Piermatti, F. Pizzo, L. Vaccaro, Synthesis, 2012, 44, 2181-2184.
Imidazolinium salts are capable of catalysing an aza-Diels-Alder reaction with a range of imines and Danishefsky's diene, leading to the desired products in good to excellent yields.
V. Jurcik, R. Wilhelm, Org. Biomol. Chem., 2005, 3, 239-244.
An enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy allows excellent stereocontrol during cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.
N. Gouault, M. Le Roch, A. Cheignon, P. Uriac, M. David, Org. Lett., 2011, 13, 4371-4373.
A gold-catalyzed cyclization of β-amino-ynone intermediates and halodeauration process enables a rapid and efficient one-step halopyridone synthesis.
K. H. Nguyen, S. Tomasi, M. Le Roch, L. Toupet, J. Renault, P. Uriac, N. Gouault, J. Org. Chem., 2013, 78, 7809-7815.