Categories: C-N Bond Formation >
Synthesis of urea derivatives
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Recent Literature
Structurally and functionally diverse N-carbamoylamino acids were
obtained through the alkylation of monosubstituted parabanic acids followed by
hydrolysis of the intermediate products in very good yields and excellent purity.
A. V. Bogolubsky, S. V. Ryabukhin, G. G. Pakhomov, E. N. Ostapchuk, A. N.
Shivanyuk, A. A. Tolmachev, Synlett, 2008,
2279-2282.
Pd-catalyzed arylation of ureas enables a facile synthesis of an array of
unsymmetrical N,N′-diarylureas in good to excellent yields from
benzylurea via a one-pot arylation-deprotection protocol, followed by a second
arylation.
S. Breitler, N. J. Oldenhuis, B. P. Fors, S. L. Buchwald, Org. Lett., 2011,
13, 3262-3265.
Palladium-catalyzed amidation allows the preparation of unsymmetrically
substituted ureas. Both aryl bromides and chlorides, as well as heteroaryl
chlorides, have been coupled to aryl, benzyl, and aliphatic ureas by using a
novel nonproprietary bipyrazole ligand (bippyphos).
B. J. Kotecki, D. P. Fernando, A. R. Haight, K. A. Lukin, Org. Lett., 2009,
11, 947-950.
The arylation of N-H and O-H containing compounds at room temperature with
phenylboronic acids is promoted in the presence of cupric acetate and a tertiary
amine. Substrates include phenols, amines, anilines, amides, imides, ureas,
carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett.,
1998, 39, 2933-2936.
A mild, ruthenium-catalyzed anti-Markovnikov addition of secondary amides,
anilides, lactames, ureas, bislactames, and carbamates to terminal alkynes
has been developped. Two complementary protocols provide either the E
or the Z isomers.
L. J. Goossen, J. E. Rauhaus, G. Deng, Angew. Chem. Int. Ed., 2005,
44, 4042-4045.
Imidazolidin-2-ones are prepared in two steps from readily available N-allylamines.
Addition of the amine starting materials to isocyanates affords N-allylureas,
which are converted to imidazolidin-2-ones with generation of two bonds and
up to two stereocenters in the presence of aryl bromides, a catalytic amount
of Pd2(dba)3/Xantphos and NaOtBu.
J. A. Fritz, J. S. Nakhla, J. P. Wolfe, Org. Lett.,
2006,
8, 2531-2534.
