Green and novel protocol for one-pot synthesis of-acetamido carbonyl compounds using Mn(bpdo)2Cl2/MCM-41 catalyst

Article abstract of DOI:10.1080/00397910903051267

Aromatic aldehydes were reacted in a one-pot reaction with enolizable ketones, acetonitrile, and acetyl chloride in the presence of Mn(bpdo) ₂Cl₂/MCM-41 under reflux condition or at 80°C to afford the corresponding β-acetamido ketones in good yields.

Full text of DOI:10.1080/00397910903051267

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Green and Novel Protocol for One-Pot
Synthesis of β-Acetamido Carbonyl
Compounds Using Mn(bpdo)2Cl2/MCM-41
Catalyst
Majid M. Heravi a , Mansoureh Daraie a , Farahnaz K. Behbahani b
Reihaneh Malakooti c
&
a Department of Chemistry, School of Sciences, Azzahra University,
Vanak, Tehran, Iran
b Department of Chemistry, School of Sciences, Azad University,
Karaj Branch, Karaj, Iran
c Department of Chemistry, University of Birjand, Birjand, South
Khorasan, Iran
Published online: 12 Mar 2010.
To cite this article: Majid M. Heravi , Mansoureh Daraie , Farahnaz K. Behbahani & Reihaneh
Malakooti (2010): Green and Novel Protocol for One-Pot Synthesis of β-Acetamido Carbonyl
Compounds Using Mn(bpdo)2Cl2/MCM-41 Catalyst, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 40:8, 1180-1186
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Synthetic Communications1, 40: 1180–1186, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903051267
GREEN AND NOVEL PROTOCOL FOR ONE-POT
SYNTHESIS OF b-ACETAMIDO CARBONYL
COMPOUNDS USING Mn(bpdo)2Cl2/MCM-41
CATALYST
Majid M. Heravi,1 Mansoureh Daraie,1
Farahnaz K. Behbahani,2 and Reihaneh Malakooti3
1Department of Chemistry, School of Sciences, Azzahra University,
Vanak, Tehran, Iran
2Department of Chemistry, School of Sciences, Azad University,
Karaj Branch, Karaj, Iran
3Department of Chemistry, University of Birjand, Birjand,
South Khorasan, Iran
Aromatic aldehydes were reacted in a one-pot reaction with enolizable ketones, acetonitrile,
and acetyl chloride in the presence of Mn(bpdo)2Cl2/MCM-41 under reflux condition or at
80 ꢀC to afford the corresponding b-acetamido ketones in good yields.
Keywords: b-Acetamido carbonyl compounds; heterogeneous catalysis; Mn(bpdo)2Cl2=MCM-41
Multicomponent reactions (MCRs) are a promising and vital field of chemistry
because they are rapid and efficient and can synthesize complicated molecules with-
out isolation of any intermediate. They require minimum effort, which minimizes
environmental loading and is acceptable from a green chemistry point of view.
The synthesis of b-acetamido carbonyl compounds has gained considerable attention
in organic synthesis. The b-acetamido carbonyl skeletons exist in a number of biolo-
gically or pharmalogically important compounds.[1,2] The best known procedure for
the synthesis of these compounds is the Dakin–West reaction,[3] which involves the
condensation of an a-amino acid with acetic anhydride in the presence of a base via
an azalactone intermediate.[4] Iqbal and coworkers introduced both CoCl2 and
[5]
montmorillonite K-10 clay[6] catalyzed MCRs involving an aldehyde, enolizable
ketone, or keto ester in acetonitrile and acetyl chloride for the one-pot synthesis
of b-acetamido carbonyl compounds. Afterward, a number of catalysts such
as Cu(OTf)2=Sc(OTf)3,[7] silica-supported sulfuric acid,[8] BiOCl,[9] ZrOCl2 ꢁ
8H2O,[10] H6P2W18O62,[11] H3PW12O40,[12] I2,[13] Amberlyst-15,[14] CeCl3 ꢁ 7H2O,[15]
Received April 12, 2009.
Address correspondence to Majid M. Heravi, Department of Chemistry, School of Sciences,
Azzahra University, Vanak, Tehran, Iran. E-mail: mmh1331@yahoo.com
1180

b-ACETAMIDO CARBONYL COMPOUNDS
1181
Scheme 1. R1 ¼ H, 4-nitro, 3-nitro, 4-methyl, 4-methoxy, 4-chloro; R2 ¼ H, 4-nitro.
and FeCl3 ꢁ 6H2O[16] were reported as effective catalysts for the synthesis of
b-acetamido carbonyl compounds.
Herein, we report an important three-component reaction in the presence of
Mn(bpdo)2Cl2=MCM-41 as a green and nano-catalyst. b-Acetamido carbonyl
compounds were synthesized using Mn(bpdo)2Cl2=MCM-41, aromatic aldehydes
derivatives, acetophenone, acetyl chloride, and acetonitrile under reflux conditions
(Scheme 1).
Previously, MCM-41 had been used in several organic transformation such as
MCM-41-supported bidentate phosphine palladium(0) complex for the Sonogashira
reaction of aryl iodides,[17] Al-MCM-41 for N-alkylation of aniline,[18] anchored
palladium bipyridyl complex in nanosized MCM-41 for the Kumada–Corriu reac-
tion,[19] vapor-phase oxidation of tetralin over Cr- and Fe-substituted MCM-41 mol-
ecular sieves,[20] MCM-41-supported bidentate phosphine palladium(0) complex for
the heterogeneous Suzuki reaction,[21] and 12-tungstophosphoric acid supported on
MCM-41 for esterification of fatty acid.[22] Recently, Mn-MCM-41 has been also
used as catalyst[23] for hydroxylation of benzene,[24] the oxidation of ethyl benzene
to acetophenone,[28] the oxidation of cyclohexene to cyclohexenol and cyclohexe-
none,[29] and oxidative aromatization of Hantzsch 1,4-dihydropyridines[30] and
epoxidation of styrene and stilbene.[32]
RESULTS AND DISCUSSION
First, to optimize of the best reaction conditions, we set up a model reaction with
benzaldehyde (1 mmol), acetophenone (1 mmol), acetyl chloride (1.5 mmol), and acet-
onitrile (0.05 mL). Results of 50% yield occurred at 4.0, 6.0, and 8.0 h and at 80 ꢀC.
Increasing the time just promoted the synthesis of chalcone (entries 1–3, Table 1).
By changing conditions (5 mL of acetonitrile, 4.0 h, reflux), we obtained b-acetamido
carbonyl compound=chalcon in 80=5% and 80=10% yields (entries 4 and 5, Table 1). In
these cases, prolonged reaction times did not affect the yield of b-acetamido carbonyl
compound. The use of 2 and 0.5 mL of acetonitrile (entries 6 and 7, Table 1) gave simi-
lar results. Therefore, entry 7 of Table 1 was chosen as the optimized reaction.
In optimized reaction conditions, various aldehydes with electron-donating
and electron-withdrawing groups and enolized ketones such as acetophenone and
4-nitro acetophnone were subjected to the one-pot, three-component synthesis of
b-acetamido carbonyl compounds in the presence of Mn(bpdo)2Cl2=MCM-41 under
solvent-free conditions (Table 2). The naturality of groups did not affect the reaction

1182
M. M. HERAVI ET AL.
Table 1. Optimization of reaction conditions using benzaldehyde (1 mmol), acetophenone (1 mmol), and
acetyl chloride (1.5 mmol) in the presence of various amounts of acetonitrile
Entry
CH3CN(mL)
Temp. (ꢀC)
Time (h)
Yielda (%) of chalcone=product
1
2
3
4
5
6
7
0.05
’’
80
’’
4.0
6.0
8.0
4.0
7.0
4.0
’’
20=50
30=50
40=50
5=80
’’
’’
Reflux
5
’’
’’
’’
’’
10=80
5=80
5=80
2
0.5
aYields refer to the isolated pure products.
times and yields. The reaction with methyl aceto acetate was also made instead of
acetophenone derivatives. The results are shown in Table 2.
In summary, we have revealed a simple, efficient, and green protocol for the
preparation of b-acetamido carbonyl compounds using Mn(bpdo)2Cl2=MCM-41
as a reusable catalyst. The salient features of this protocol include operational sim-
plicity, excellent yields of the products, avoidance of column chromatography, ready
availability, low toxicity, and reusability of the catalyst.
EXPERIMENTAL
All the chemicals were purchased from Merck Company. Melting points were
measured by using the capillary tube method with an Electrothermal 9200 apparatus.
1H NMR spectra were recorded on a Bruker AQS Avance 300-MHz spectrometer
using tetramethylsilane (TMS) as an internal standard (CDCl3 solution). Infrared
(IR) spectra were recorded on the Fourier transform (FT)-IR Bruker Tensor 27.
All products were known compounds and identified by comparison of their spectral
and physical data to the literature description (Table 2).
Table 2. Preparation of b-acetamido carbonyl compounds from aldehydes and enolizable ketones in the
presence of acetyl chloride and acetonitrile catalyzed using Mn(bpdo)2Cl2=MCM-41
Mp (ꢀC)
Entry
Aldehyde
Benzaldehyde
Ketone
Time (h) Yield (%)a Observed
Found
1
2
Acetophenone
’’
4.0
4.0
4.15
3.0
3.0
3.2
3.5
4.0
4.3
3.5
87
78
79
85
85
78
80
85
85
75
105–106 102–104[38]
149–151 148–149[39]
115–117 112–115[38]
4-Nitro benzaldehyde
3-Nitro benzaldehyde
4-Methyl benzaldehyde
Benzaldehyde
3
’’
4
’’
4-Nitro acetophenone
113–115
75–77
84–86
112[39]
5
74–76[38]
83–85[38]
87–89[38]
6
4-Methyl benzaldehyde
4-Methoxy benzaldehyde
4-Chloro benzaldehyde
Benzaldehyde
’’
7
’’
88–90
8
’’
121–122 116–118[38]
136–138 129–131[40]
137–139 130–132[40]
9
10
Methyl aceto acetate
’’
4-Chloro benzaldehyde
aYields refer to the isolated pure products.

b-ACETAMIDO CARBONYL COMPOUNDS
1183
Preparation of MCM-41
MCM-41 was prepared according to the procedure described.[23,31,33–35]
Synthesis of bpdo Ligand
2,20-Bipyridine-1,10-dioxide was prepared according to the procedure reported
by Simpson and coworkers.[36]
Synthesis of Mn(bdpo)2Cl2
This compound was prepared according to the procedure described
previously.[36]
Immobilization of Mn(bdpo)2Cl2 Nanoreactors of MCM-41
Mn(bdpo)2Cl2 (0.2 g) in 5 mL of ethanol was slowly added to a solution of 1 g
of MCM-41 in 5 mL of ethanol. The resultant mixture was refluxed for 24 h under
nitrogen gas. Upon filtration of the mixture, the solid was washed with ethanol.
The atomic absorption spectrophotometry (AAS) determination showed the percen-
tages of Mn and Cl were 4.4 and 5.72, respectively.[37]
Synthesis of b-Acetamido Ketone and Esters: General Procedure
A mixture of ketone or methyl aceto acetate (5 mmol), aldehyde (5 mmol), and
acetyl chloride (1.5 mL) in aceto nitrile (0.5 mL) was treated with a catalytic amount
of Mn(bpd)=2 (1 mol%) at 80 ꢀC. The progress of the reaction was monitored by
thin-layer chromatography (TLC). Upon completion of the reaction, ice water was
added to the reaction mixture. The precipitate was obtained for some derivatives.
After filtration, the residue was washed with diethyl ether (10 mL) and the catalyst
was removed. After evaporating the solvent, the crude product was crystallyzed with
ethanol–water or n-hexane–ethyl acetate. For some cases in which a solid was not
obtained, we solved them in petroleum ether and put them in a refrigerator over-
night. Over time, we observed a solid and filtered and collected the product.
For the other derivatives, after adding ice water, the oily products were
obtained, extracted with dichloromethane (10 mL), and dried, and the solvent was
evaporated under reduced pressure.
To investigate the reusability and recyclibility of the catalyst, the catalyst
was washed using diethyl ether and dried. The recycled catalyst could be subjected
in subsequent experiments and gave similar results (76, 74, 75%).
Spectroscopic Data for Some Compounds
b-Acetamido-b-(phenyl)propiophenone (Table 2, Entry 1). IR (KBr)
1
n
max=cmꢂ1: 3286, 1693, 1650; H NMR (300 MHz; CDCl3) dH 2.1 (s, 3H, CH3),
3.49 (dd, J ¼ 6.2 and 16.9 Hz, 1H, CH2), 3.77 (dd, J ¼ 5.3 and 16.9 Hz, 1H, CH2),
5.61 (m, 1 H, methyne H), 6.92 (br, d, J ¼ 6.3 Hz, 1H, NH), 7.25–7.60 (m, 8H,

1184
M. M. HERAVI ET AL.
Ar-H), 7.94 (d, J ¼ 7.5 Hz, 2H, Ar-H), dc (100 MHz, CDCl3) 23.6, 43.2, 49.9, 126.6,
127.7, 128.3, 128.9, 133.7, 136.4, 140.7, 169.3, 198.3.
b-Acetamido-b-(4-nitrophenyl)propiophenone (Table 2, Entry 2). IR
1
(KBr) nmax=cmꢂ1: 3291, 1689, 1653; H NMR (300 MHz; CDCl3) dH 2.05 (s, 3 H,
CH3), 3.38 (dd, J ¼ 5.8 and 17.4 Hz, 1 H, CH2), 3.85 (dd, J ¼ 7.1 and 17.4 Hz, 1
H, CH2), 5.64 (m, 1H, methyne H), 7.19–7.54 (m, 7H, Ar-H) 7.80 (d, J ¼ 7.7 Hz,
2H, Ar-H), 9.10 (br, 1H, NH). dc (100 MHz, CDCl3) 23.5, 42.6, 49.2, 123.7, 127.2,
127.9, 128.7, 131.0, 133.9, 136.0, 138.4, 169.5, 197.8.
b-Acetamido-b-(3-nitrophenyl)propiophenone (Table 2, Entry 3). IR
1
(KBr) nmax=cmꢂ1: 3291, 1689, 1653; H NMR (300 MHz; CDCl3) dH 2.12 (s, 3 H,
CH3), 3.55 (dd, J ¼ 5.5 and 17.6 Hz, 1 H, CH2), 3.73 (dd, J ¼ 5.0 and 17.5 Hz, 1
H, CH2), 5.70 (m, 1H, methyne H), 7.21 (d, J ¼ 7.6 Hz, 1H, NH), 7.46–7.58 (m,
3H, Ar-H), 7.65 (t, J ¼ 7.4 Hz, 1H, Ar-H), 7.76 (d, J ¼ 7.5 Hz, 1H, Ar-H), 7.91(d,
J ¼ 8.3 Hz, 2H, Ar-H), 8.14(d, J ¼ 8.3 Hz, 1H, Ar-H), 8.26(s, 1H, Ar-H). dc
(100 MHz, CDCl3) 23.6, 42.9, 49.3, 121.5, 122.6, 128.3, 129.1, 129.8, 130.8, 133.1,
134.2, 136.4, 143.7, 169.9, 198.3.
ACKNOWLEDGMENT
M. M. H. and F. K. B. are thankful to the presidential office for partial
financial assistance under Project No. 87066=26.
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