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182 Chemistry and Biology of Beta-Lactams
Sonication
O
Z
2
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5.15.1 Microwave- and Ultrasound-Induced Heck Reaction
Toward Polycyclic Beta-Lactams
The above unsaturated beta-lactams underwent Heck type of cyclization in the presence of palladium
reagent in a microwave or an ultrasound. Polycyclic beta-lactams were assembled using this method
(Scheme 5.36) [93].
5.16 Microwave- and Ultrasound-Induced Synthesis of Ferrocenyl β-Lactams
A stereospecic synthesis of a few trans-3,4-disubstituted β-lactams using polyaromatic ferrocenyl
imines by Staudinger reaction was investigated [94] (Scheme 5.37). We reported the reaction of polyaromatic imines with acid chlorides and formation of trans-β-lactams. Some of the trans-β-lactams demonstrated anticancer activity [95–97]. A few compounds were active against diverse cancer cells in vivo
with appropriate therapeutic index and minimum toxicities.
Although numerous benzene-derived aldehydes were used as starting materials for the preparation of imines, the use of ferrocene aldehyde as one of the components for imine preparation was not
investigated.
Reaction of ferrocene aldehyde with polyaromatic amines produced imines (Ta ble 5.3). The imine
was then reacted with acid chloride, and a trans-β-lactam was obtained. This result was similar to that
obtained when an aromatic phenyl or substituted phenyl group was present in the imine component. In
Pd(OAc)
Br
N
SCHEME 5.36 Microwave- and Ultrasound-Induced Heck Cyclization Toward Polycyclic Beta-Lactams.
N
Fe
N
H
Fe
Fe
MW
or
N
Fe
N
H
Z
2
N
O
H
CH
N
H
Fe
N
H
Fe
SCHEME 5.37 Examples of Ferrocenyl Imines.
TABLE 5.3
R
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Preparation of Ferrocenyl Imines
Entry R
1 1-Napthylamine Scheme 37 85%
2 1-Aminoanthracene Scheme 37 80%
3 6-Amino chrysene Scheme 37 75%
4 9-Aminophenantherene Scheme 37 78%
5 11-Dibenzofulleorene Scheme 37 75%
6 1-Aminopyrene Scheme 37 75%
N
H
Fe
SCHEME 5.38 Synthesis of trans-Ferrocenyl-Beta-Lactams by Microwave or Ultrasound.
+
R
1
COCl
N
Et
3
3-Ferrocinyl imine
(3a-f) Yield
1
R
HH
O
Fe
N
R
O
a
1
R
O
+
O
TABLE 5.4
Synthesis of Beta-Lactams with Ferrocene
Entry R
1 OAc 1-Napthyl amine 100:0 5–6 min 85%
2 OAc 1-Aminoanthracene 100:0 5–6 min 85%
3 OAc 6-Aminochrysene 100:0 6–7 min 80%
4 OAc 9-Aminophenantherene 100:0 6–7 min 80%
5 OAc 11-Dibenzofulleorene Aminodibenzofullorene 100:0 6–7 min 80%
6 OBn 1-Napthyl amine 100:0 5–6 min 85%
7 OBn 1-Aminoanthracene 100:0 5–7 min 85%
8 OBn 6-Aminochrysene 100:0 6–7 min 80%
9 OBn 9-Aminophenantherene 100:0 6–7 min 80%
10 OBn 11-Di benzo fulle orene Amino diben zoful loren e 100:00 6–7 min 80%
1
R
Diastereomeric
(rato) Time (mi) Yield
183Microwave and Ultrasound in Beta-Lactam Chemistry
HH
Fe
N
R
a similar way, cycloaddition with imines produced exclusively trans-phthalimido β-lactams. No cisphthalimido β-lactams were formed (Scheme 5.38 and Table 5.4).
The ferrocenyl group at the C part of the imine behaved like an aromatic group rather than a conjugated aromatic system. It was found that the conjugated part of the imines altered the stereochemical
proportion of the β-lactams. The iron present in ferrocene failed to stabilize the intermediate that produces cis-compounds. An availability of these compounds may prove useful for structure–activity study.
5.17 Microwave-Induced Bismuth Nitrate-Catalyzed Michael
Reaction of 3-Amino Beta-Lactams with Enones
Aza-Michael reaction is an important method for the formation of C–N bond. This reaction was used to
access numerous medicinally active molecules like antibiotics, anticancer, amino acids, and peptides.
The cis-amino β-lactams are the current antibiotics. Similar structures with trans-conguration are also
184 Chemistry and Biology of Beta-Lactams
O
donor
EWG
Z
H
Z=
6
6
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available. A microwave-induced bismuth nitrate-catalyzed Michael reaction of 3-amino β-lactam with
unsaturated ketone was available.
Despite progress in β-lactam research, no information was published that described functionalization
of the 3-amino group present in the β-lactam ring through a catalytic Michael reaction. A simple and
environmentally benign procedure to obtain mono- and bis-aza-substituted β-lactams was developed
under microwave and ultrasonic condition.
Our research group performed aza-Michael reaction of aliphatic and aromatic amines to unsaturated
enones via bismuth nitrate-catalyzed reaction. The scope of this reaction was extended using amino
β-lactams.
The starting material for the Michael reaction was racemic 3-amino β-lactams. Synthesis of amino
β-lactams was done by deprotecting the phthalimido group in β-lactam using ethylene diamine in a
microwave (Scheme 5.39).
The racemic trans-3-amino β-lactam was reacted with methyl vinyl ketone in the presence of bismuth
nitrate in THF as the solvent under microwave condition (Scheme 5.40). The reaction mixture was heated
for 2–6 min in a microwave reactor [98]. The reactions proceeded, and the products were obtained along
with substantial amount of bis-aza-adduct in good yield. Regardless of reaction time, catalyst amount,
and molar ratios of the acceptor, mono-aza-adduct was not formed selectively.
The method was then extended to chiral 3-amino β-lactams. The enantiopure 3-amino β-lactams were
obtained by our method (Scheme 5.41). First phthalimido beta-lactams were prepared.
An excellent stereoselectivity was observed, and the reaction produced a single compound with a
conguration of (3R,4R) as the major products. The N-phthalimido functionality in the β-lactams was
deprotected to obtain the optically active 3-amino beta-lactams (Scheme 5.42).
The 3-amino-β-lactam was reacted with methyl vinyl ketone under microwave with bismuth nitrate
for 3–5 min. The reaction proceeded well with excellent yield (Scheme 5.43). The aza-Michael reaction
EWG
NH
2
R
2
N
R
1
Michael
SCHEME 5.39 Bismuth Nitrate-Catalyzed Aza-Michael Reaction Under Microwave and Sonication.
SCHEME 5.40 Aza-Michael Reaction Under Microwave.
COOH
SCHEME 5.41 Asymmetric Staudinger [2+2] Ketene-Imine Cycloaddition Reaction.
+
NtPh
EWG
Michael
acceptor
+
=
R
Bi(NO3).5H
O
H
(S)
N
R
Ph, PMP,
MW
O
4-Me.C
GWE
O
2
Et
H
-,4-X.C
4
3
Mukaiyama
O
mono-adduct
N
reagent
H
H
N
+
R
2
N
R
1
HH
Z
(R)(R)
N
O
-
etc
4
N
O
O
(S)
R
R
2
N
R
1
O
185Microwave and Ultrasound in Beta-Lactam Chemistry
GWE
H
GWE
EWG
O
R
N-phthalimido(-NtPh)
(R
H
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H
O
H
H
Z
O
Z
SCHEME 5.42 Deprotection of N-Phthalimido Group Under Microwave Irradiation.
NH
2
H
(R)
O
N
R
=
1
SCHEME 5.43 Aza-Michael Reaction of Nitrile and Ester Under Microwave.
H
(R)
(s)
O
(s)
O
O
)
=
N
(R)
R
(s)
O
EWG
Bi(NO3).5H
MW
NH
2
O
2
MW
.CH2CH
2
solventless
.NH
O
(R)
H2N
(R)
2
O
N
R
N
(R)
R
O
H
H
(s)
(R)
O
N
R
N
1
(R)
+
O
1
R
N
(R)
R
with optically active β-lactam amines produced mono-aza-adduct predominantly over the bis-adduct.
The best selectivity was obtained when the substrate had a p-methoxyphenyl group at N1 position. The
results suggested that electron-withdrawing groups at nitrogen lower the selectivity.
The electron-withdrawing functionality in aromatic system took longer time to have the product. THF
and dichloroethane were found to be good solvent systems for this method. A small portion of the catalyst (1.0–1.5 mmol) was used. The irradiation time was 2–10 min in an automated microwave. A few
other bismuth salts were not efcient in pursuing the Michael reaction of these amino β-lactams. For
instance, bismuth chloride, bismuth iodide, and bismuth chloride were not effective: about 20% yield of
the products was obtained.
The sensitivity of the β-lactam prohibited the use of stronger acids in performing Michael reaction
successfully. For example, HCl, SnCl4, BF3.Et2O, AlCl3, and Et2AlCl2 were not efcient. Importantly,
the reactions were performed in the presence of moisture and did not require inert atmosphere. A coordination of the empty d-orbital of the bismuth with the electron pair of oxygen of the ketone and ester
was responsible for the nucleophilic attack. This method required about 10 mol% of bismuth nitrate. The
reaction proceeded in concentrated solution.
5.18 Microwave-Induced Reactions: The Effects of Tan δ
and Dipole Moments in β-Lactam Chemistry
The low tan δ values of the solvents were more efcient than solvents with high dipole and dielectric constants in microwave-induced reactions. No reports were available on the tan δ values of the solvents used
in microwave-induced reactions of β-lactams. During our investigations on β-lactams and microwave,
we realized that solvents have a critical role in many processes. The synthesis of hydroxy-β-lactams in a
domestic microwave with diverse solvents focusing on the tan δ values was investigated.
The preparation of optically active β-lactams with different aromatic groups (p-anisyl, phenyl, tolyl,
and benzyl) under microwave irradiation was conducted (Scheme 5.44). The reaction of benzyloxyacetyl
chloride and Schiff base in the presence of N-methylmorpholine in different solvents produced a chiral
β-lactam using the Staudinger reaction. Several solvents were investigated to optimize the best condition.
The reaction was conducted in a microwave oven with ethylene dichloride, and β-lactams were produced. The tan δ values of the solvents were examined to know their effects [99].
186 Chemistry and Biology of Beta-Lactams
’
PhCH
O
O
Ethylene
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OCH2COCl
2
SCHEME 5.44 Synthesis of Optically Active Beta-Lactams.
TABLE 5.5
Tan δ Values of Solvents in the Microwave Field at 2.45 GHz and 20°C
Solvent tan δ Solvent tan δ Solvent tan δ
Ethylene glycol 1.35 2-Butanol 0.44 Chloroform 0.09
Ethanol 0.94 Dichlorobenzene 0.28 Acetonitrile 0.06
DMSO 0.82 NMP 0.27 Ethyl acetate 0.05
2-Propanol 0.79 Acetic acid 0.17 Acetone 0.05
Formic acid 0.72 DMF 0.16 THF 0.04
Methanol 0.65 Dichloroethane 0.12 Dichloromethane 0.04
Nitrobenzene 0.58 Water 0.12 Toluene 0.04
1-Butanol 0.57 Chlorobenzene 0.10 Hexane 0.02
+
H
O
N
Ar
N-methylmorpholine,
MW
dichloride
PhH
2
H H
CO
H
O
N
Ar
O
In order to be adequately heated in a microwave, a material should have dielectric properties [100 –
109]. Importantly, the dielectric and dipole moment values of the solid surfaces and solvents used in
the reactions along with the charge density of the nal compounds affect the course of the reactions as
well as the biological activities of the products. Under a microwave, the heating properties of a material
depended on the process of converting electromagnetic power into heat energy. The ability of this process was expressed using a parameter called tan δ (the loss tangent). The tan δ values of a few solvents
are given in Table 5. 5. For a rapid heating, a high tan δ was required for a solvent. But solvents with low
tan δ values were also useful in microwave-induced reactions. The substrates or reagents/catalysts must
be polar, and the average dielectric properties of a reaction contents should permit sufcient heating by
microwave. So, microwave heating can be possible with a nonpolar solvent under a specic situation.
Moreover, if the reaction mixture is nonpolar, passive heating is added to help the heating method.
tan
ε’’=dielectric loss (indicates the efciency by which electromagnetic radiation is transformed into heat);
ε’=dielectric constant (polarizable power of molecules in the presence of the electric eld)
The tan δ values of a few solvents were available. The role of tan δ was evaluated in order to explain
their effects in the β-lactam synthesis. For example, dichloromethane with tan δ 0.042 was able to produce a lactam after 5 min of microwave exposure at 40ºC. In contrast, the reaction was not completed
when toluene with tan δ 0.04 was used at 80ºC after 10 min of irradiation. It was found that solvents with
lower tan δ values are effective. Table 5.6 shows the tan δ values, dipole moment, and dielectric constant
of some solvents.
Acid chloride (or an equivalent), intermediate ketene, Schiff base, and product were able to react with
alcoholic solvents, water, acetone, and acetonitrile. The undesirable reactions were predominant, and
this had limited their use in the preparation of β-lactams. Hydrocarbon solvents, for example toluene
(tan δ=0.04) and xylene (tan δ=0.04), failed to produce products in good yield despite their low tan δ
values. The dipole moment and dielectric constant values of toluene and xylene were also low. DMF
was efcient because of low tan δ (ta n δ=0.16) and high dipole moments, and dielectric properties. This
work indicated that for the preparation of β-lactams, solvents with low tan δ and high dipole moment and
high dielectric constant are required. A lower tan δ value of solvents was able to control the yield of the
product even more than the solvent’s high dielectric constant. For example, dichloroethane (tan δ= 0.12),
’’
TABLE 5.6
0
2
3
5
6
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Approximate Tan δ Values of Solvents in the Microwave Field
at 2.45 GHz and 20°C, Dipole Moment, and Dielectric Constant
Solvent tan δ Dipole moment Dielectric constant
Ethylene glycol 1.35 2 37
Ethanol 0.94 1.7 24
Methanol 0.66 1.7 33
Water 0.12 1.8 80
Ethyl acetate 0.06 1.78 6
Acetone 0.05 2.9 21
1,2-Dichloroethane 0.13 1.8 10
Dichloromethane 0.04 1.5 8
THF 0.05 1.6 7
Toluene 0.04 0.4 2.4
Acetonitrile 0.06 3.9 36
DMSO 0.82 3.9 47
DMF 0.16 3.8 38
Xylene 0.04 0.6 2.6
187Microwave and Ultrasound in Beta-Lactam Chemistry
6
5
4
3
2
1
0
tan
Axis Title
FIGURE 5.4 Ta n δ, dipole moment, and dielectric constant of organic solvents.
90
80
70
60
50
40
30
20
10
Dielectric constant
0
dichloromethane (tan δ=0.04), and tetrahydrofuran (tan δ=0.04) were more efcient than DMSO (tan
δ=0.82) and DMF (tan δ=0.16). The DMSO and DMF had tan δ, but comparable dipole moment. Figure
5.4 indicates the tan δ values, dipole moment, and dielectric constant values of a few solvents.
5.19 Conclusion
Microwave- and ultrasound-assisted methods have become very efcient in the synthesis of diverse
β-lactams in chiral and achiral forms. These reactions are conducted in liquid phase and also using
solids. The dipole moment, dielectric constant, and penetration depth have inuence in the described
methods. Many of these stereocontrolled processes are conducted without using solvents. Most of the
reactions were completed within a few minutes. Notably, optically active complex polycyclic β-lactam
structures are prepared using these methods.
188 Chemistry and Biology of Beta-Lactams
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Acknowledgments
AD is grateful to CEA-Grenoble, Joseph Fourier University, University of Göttingen, and University of
California, Los Angeles, for their support. BKB is grateful to the US NIH, the US NCI, Texas Kleberg
Foundation, Stevens Institute of Technology, University of Texas MD Anderson Cancer Center, University
of Texas-Pan American, and Community Health Systems of Texas for their nancial and moral support
to his research. AD and BKB are also grateful to their current employer, Prince Mohammad Bin Fahd
Un iversit y.
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