Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles >
Synthesis of oxazolidinones and derivatives
Recent Literature
Synthesis of oxazolidin-2-ones derivatives was carried out starting from urea
and ethanolamine reagents using microwave irradiation in a chemical paste medium
in which a catalytic amount of nitromethane absorbs the microwaves and generates
hot spots.
G. Bratulescu, Synthesis, 2007,
3111-3112.
An efficient, versatile and practical gram-scale preparation of
oxazolidinone, imidazolidinone and dioxolanone is achieved.
N. Alouane, A. Boutier, C. Baron, E. Vrancken, P. Mangeney, Synthesis, 2006, 860-864.
An efficient sequential intramolecular cyclization of amino alcohol carbamates
followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions
gives N-aryl oxazolidinones in good yields. The reaction tolerated aryl
iodides containing functionalities such as nitriles, ketones, ethers, and
halogens. Heteroaryl iodides and substituted amino alcohol carbamates were can
also be transformed.
W. Mahy, P. K. Plucinski, C. G. Frost, Org. Lett.,
2014,
16, 5020-5021.
Carbonylimidazole derivatives are highly active acylation reagents for
esterification and amidation in the presence of pyridinium salts as catalysts.
These reactions are thought to involve both Brønsted acid and nucleophilic
catalysis. This mode of activation has been applied to the synthesis of
difficult to access oxazolidinones, as well as esters and amides.
S. T. Heller, T. Fu, R. Sarpong, Org. Lett., 2012,
14, 1970-1973.
A mild Pd-catalyzed ring-opening cyclization
reaction of 2-vinylaziridines with an ambient atmosphere of carbon dioxide gives
5-vinyloxazolidinones in high yield as well as regio- and
stereoselectivity.
F. Fontana, C. C. Chen, V. K. Aggarwal, Org. Lett., 2011,
13, 3454-3457.
An oxidative cleavage of alkyl C-Pd bond by H2O2 enables a
palladium-catalyzed intramolecular aminohydroxylation to give various
heterocycles with good yields and excellent diastereoselectivities. Facile
transformation of these products provided a powerful tool toward the synthesis
of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies
revealed that a SN2 type attack of water at a high-valent Pd center
is involved.
H. Zhu, P. Chen, G. Liu, J. Am. Chem. Soc., 2014,
136, 1766-1769.
The use of Pd(OAc)2 and n-Bu4NOAc as catalysts
enables ane efficient and simple synthesis of oxazolidinones, oxazolidinthiones,
imidazolidinthiones, and imidazolidinones from the corresponding propargylic
starting materials in DCE at room temperature.
S. K. Alamsetti, A. K. Å. Persson, J.-E. Bäckvall, Org. Lett., 2014,
16, 1434-1437.
A mild and efficient gold(I)-catalyzed rearrangement of propargylic tert-butylcarbamates
allows the synthesis of various 5-methylene-1,3-oxazolidin-2-ones, which would
be less conveniently obtained using other methods.
A. Buzas, F. Gagosz, Synlett, 2006,
2727-2730.
Various N-Boc-protected alkynylamines are converted into the
corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild
reaction conditions in the presence of a cationic Au(I) complex in high
yield regardless of the substitution at nitrogen and alkyne terminus.
R. Robles-Machin, J. Adrio, J. C. Carretero, J. Org. Chem., 2006, 71, 4951-4955.
A nickel-catalyzed cycloaddition of aziridines with isocyanates proceeded
smoothly to give iminooxazolidine derivatives in good yields. A longer
reaction time allowed the isomerization of the iminooxazolidine to the
corresponding imidazolidinone derivatives.
T. Munegumi, I. Azumaya, T. Kato, H. Masu, S. Saito, Org. Lett.,
2006, 8, 379-382.
2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one is a solid stable
carbonyl source that is a recyclable. The reagent enables the synthesis of
benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and
benzo[d]imidazol-2(3H)-ones using in one pot out under neutral or
acidic conditions to give the corresponding heterocycles in very good yields.
K. E. Ryu, B. R. Kim, G. H. Sung, H. J. Yoon, Y.-J. Yoon,
Synlett, 2015, 26, 1985-1990.
