Categories: Synthesis of N-Heterocycles, Amines >
Synthesis of cyclic amines
| Synthesis of | |||||
| Aziridines |  |
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Azetidines |  |
| Pyrrolidines |  |
Piperidines |  |
Piperazines |  |
| Morpholines |  |
Thio- morpholines |
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4-Piperidones |  |
Recent Literature
An efficient method for the N-heterocyclization of primary amines
with diols catalyzed by a Cp*Ir complex was developed. A variety of five-,
six-, and seven-membered cyclic amines were synthesized in good to excellent
yields.
K.-I. Fujita, T. Fujii, R. Yamaguchi, Org. Lett., 2004, 6,
3525-3528.
Microwave heating enables a Borrowing Hydrogen strategy to form C-N bonds from
alcohols and amines, removes the need for solvent and reduces the reaction times,
while the results are comparable with those using thermal heating.
A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, J. Org. Chem., 2011,
76, 2328-2331.
A one-pot synthesis of nitrogen-containing heterocycles from alkyl dihalides
and primary amines and hydrazines occurs under microwave irradiation via a
simple and efficient cyclocondensation in an alkaline aqueous medium.
Y. Ju, R. S. Varma, J. Org. Chem., 2006, 71, 135-141.
A mild, effective gold(I)-catalyzed hydroamination of unactivated olefins to
form protected nitrogen heterocycles has been developed. The substrate scope
is broader than in reactions realized with late-transition-metal catalyst
systems.
X. Han, R. A. Widenhoefer, Angew. Chem. Int. Ed., 2006, 45, 1747-1749.
Optically enriched N-fused
bicyclic amides and small- and medium-ring unsaturated cyclic amines can be synthesized in up to 98% ee
through Mo-catalyzed desymmetrization of
readily available achiral polyene substrates. The effects of catalyst structure,
olefin substitution, positioning of Lewis basic functional groups and ring size
are examined and discussed in detail.
E. S. Sattely, G. Alexander Cortez, D. C. Moebius, R. R. Schrock, A. H.
Hoveyda, J. Am. Chem. Soc.,
2005, 127, 8526-8533.
ROM-RCM of cyclobutenylmethylamines having an alkyne
moiety in a tether afforded
isoquinoline derivatives in good yields using a second-generation Grubbs catalyst.
M. Mori, H. Wakamatsu, K. Tonogaki, R. Fujita, T. Kitamura, Y. Sato, J. Org. Chem., 2005, 70, 1066-1069.
The GaCl3-catalyzed skeletal
reorganization of enynes is
simple and provides a diverse range of dienes in good to high yields. The
reaction of enynes
proceeds in a stereospecific manner with respect to the geometry of the olefin
moiety.
N. Chatani, H. Inoue, T. Kotsuma, S. Murai, J. Am. Chem. Soc., 2002, 124, 10294-10295
A powerful aza-Prins cyclization in combination with the Peterson-type
elimination reaction provides seven-membered unsaturated azacycles (tetrahydroazepines)
under mild reaction conditions and using iron(III) salts as sustainable
catalysts. In a single reaction step, a C-N, C-C bond and an endocyclic double
bond are formed.
V. Sinka, I. Fernández, J. I. Padrón, J. Org. Chem., 2022, 87,
11735-11742.
An efficient and regioselective Yb(OTf)3-promoted
palladium-catalyzed oxidative cyclization of γ-heteroalkenyl β-keto amides
has been developed. Under simple aerobic condition, various six-, seven-,
and eight-membered-ring N- and O-heterocycles were obtained in excellent yield.
K.-T. Yip, J.-H. Li, O.-Y. Lee, D. Yang, Org. Lett.,
2005, 7, 5717-5719.
A (pyridyl)phosphine-ligated ruthenium(II) catalyzes a diol-diamine coupling
to provide piperazines and diazepanes. The conditions tolerate different amines
and alcohols that are relevant to key medicinal platforms.
A. Nalikezhathu, A. Tam, V. Cherepakhin, V. K. Do. T. J. Williams, Org. Lett., 2023, 25,
1754-1759.
Use of the Ramberg-Bäcklund Rearrangement for the Synthesis of Medium and
Large Heterocyclic Alkenes: Stereoselective Olefin Formation
D. I. MaGee, E. J. Beck, J. Org. Chem., 2000,
65, 8367-8371.
