Isocyanide-based five-component synthesis of 2-Aryl-2-(2,3,4,5-tetrahydro- 2,4-dioxo-1H-1,5-benzodiazepin-3-yl)acetamides (=α-Aryl-2,3,4,5- tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides)

Article abstract of DOI:10.1002/hlca.201100313

An efficient and simple method for the synthesis of new 2-aryl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepin-3-yl)acetamides (=α-aryl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides) by a five-component condensation reaction of benz

Full text of DOI:10.1002/hlca.201100313

Helvetica Chimica Acta – Vol. 95 (2012)
483
Isocyanide-Based Five-Component Synthesis of 2-Aryl-2-(2,3,4,5-tetrahydro-
2,4-dioxo-1H-1,5-benzodiazepin-3-yl)acetamides (¼a-Aryl-2,3,4,5-
tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides)
by Roya Akbarzadeha), Tayebeh Amanpoura), Ali Abolhasani Soorkib), and Ayoob Bazgir*a)
a) Department of Chemistry, Shahid Beheshti University, General Campus, Tehran 1983963113, Iran
(e-mail: a_bazgir@sbu.ac.ir)
b) Research Institute of Applied Sciences, Academic Center for Education, Culture and Research,
Shahid Beheshti University, Tehran, Iran
An efficient and simple method for the synthesis of new 2-aryl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-
1,5-benzodiazepin-3-yl)acetamides
(¼a-aryl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-
acetamides) by a five-component condensation reaction of benzene-1,2-diamine (1), Meldrumꢀs acid
(2), aldehydes 3, isocyanides 4, and H2O in CH2Cl2 at room temperature is reported (Table 1 and
Scheme 2). These products were evaluated in vitro for their antibacterial activities (Table 2).
Introduction. – Within the past decade, the resurgence of interest in multi-
component reactions (MCRs) has been driven not only by their convergent nature,
superior atom economy, and straightforward experimental procedures but also because
of their value in pharmaceutical industry for the construction of low-molecular-mass
compound libraries through combinatorial design and parallel synthesis [1]. Isocya-
nide-based multicomponent reactions (IMCRs) are particularly interesting as they are
more versatile and diverse than other MCRs [2]. The great potential of isocyanides for
the development of multicomponent reactions lies in the diversity of their bond
forming processes, functional group tolerance, and the high levels of chemo-, regio-,
and stereoselectivity often observed. Moreover, there is virtually no restriction on the
nature of the nucleophiles and electrophiles in IMCRs. The MCRs involving
isocyanides have emerged as valuable tools for the preparation of structurally diverse
chemical libraries of drug-like heterocyclic compounds [3]. In this context, benzodi-
azepine derivatives show interesting features that make them attractive for the use in
IMCRs [4].
Benzodiazepines have attracted considerable interest in recent years. Its derivatives
are known to display a wide range of pharmacological activities as anticonvulsant, anti-
anxiety, analgesic, sedative, antidepressive, and hypnotic agents [5] and as anti-
inflammatory agents [6]. Some benzodiazepines also find commercial use as dyes for
acrylic fibers [7]. More recently, the area of biological interest of 1,5-benzodiazepines
has been extended to antibiotics [8], and various diseases such as cancer [9], viral
infection (HIV) [10], and cardiovascular disorders [11]. Among the 1,5-benzodiaze-
pines, the 1,5-benzodiazepin-2-ones such as lofendazam [12], telenzepine [13],
triflubazam [14], and clobazam [15] (Fig.) are clinically used as anxiolytic or
antisecretory agents. Furthermore, compound I exhibits interleukin-1b converting
ꢁ 2012 Verlag Helvetica Chimica Acta AG, Zꢂrich

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enzyme inhibition activity [16] and compound II was considered as cholecystokinin-B
receptor antagonist [17] (Fig.). Two recently published patents indicate that 2,3,4,5-
tetrahydro-1H-1,5-benzodiazepine derivatives carrying carboxamide substituents are
potentially important as therapeutic and prophylactic agents for diabetes, diabetic
nephropathy, or glomerulosclerosis [18].
Figure. Important biologically active 1H-1,5-benzodiazepines
Due to the wide range of pharmacological activity and industrial applications of 1,5-
benzodiazepines, research on this class of compounds is still very active and is directed
toward the synthesis of compounds with enhanced pharmacological activity. Generally,
these compounds are synthesized by the condensation of benzene-1,2-diamines with
a,b-unsaturated C¼O compounds, b-halo ketones, or ketones [19][20]. However, most
of these methods have their pitfalls, including severe reaction conditions as well as side-
reactions [20]. Some research has been undertaken on the benzodiazepine 3-
carboxamide derivatives. These compounds were synthesized via a multistep approach
in the presence of expensive catalysts under sensitive conditions [14 – 16]. Recently,
isocyanide-based multicomponent reactions of diamines have been applied to the
synthesis of the most important 1,5-benzodiazepines [4e – g]. Shaabani and co-workers
reported the synthesis of 2,3,4,5-tetrahydro-a-methyl-2,4-dioxo-1H-1,5-benzodiaze-
pine-3-propanamides by the three-component reaction of an aromatic diamine,
Meldrumꢀs acid (¼2,2-dimethyl-1,3-dioxane-4,6-dione), and isocyanide [4g]. Although
isocyanide-based multicomponent reactions were applied to the synthesis of various
1,5-benzodiazepines, to the best of our knowledge, no one has yet reported the
synthesis of a-aryl-tetrahydro-1H-1,5-benzodiazepine-3-acetamides which proceeds via
the formation of five new bonds (2 NꢀC þ 2 CꢀC þ CꢀO) in a five-component one-pot
reaction.
Due to the biological activity of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepines [18]
and our interest in the synthesis of heterocyclic compounds [21], we report herein an
efficient isocyanide-based five-component method for the preparation of novel 2-aryl-
2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepin-3-yl)acetamides (¼a-aryl-2,3,
4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides). These compounds

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have closely related ring systems to those of triflubazam, clobazam, and other 1,5-
benzodiazepines which have a broad spectrum of biological activities.
Results and Discussion. – The one-pot five-component condensation reactions of
benzene-1,2-diamine (1), Meldrumꢀs acid (2), aldehydes 3, isocyanides 4, and H2O
proceeded spontaneously at room temperature in CH2Cl2 and were complete after 24 h
affording the corresponding a-aryl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiaze-
1
pine-3-acetamides 5 in good yields (Table 1). H-NMR Spectra of the crude products
clearly indicated the formation of 5. All the products were characterized by IR, mass,
and 1H-NMR spectra and by elemental analysis.
Table 1. Synthesis of a-Aryl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides 5
3
Ar
4
R
Product 5
Yield [%]
3a
3b
3c
3d
3e
3f
3g
3h
3i
Ph
4a
4a
4a
4a
4a
4a
4a
4a
4b
4c
4c
4c
cyclohexyl
cyclohexyl
cyclohexyl
cyclohexyl
cyclohexyl
cyclohexyl
cyclohexyl
cyclohexyl
4-MeꢀC6H4ꢀSO2CH2
2,6-Me2C6H3
2,6-Me2C6H3
2,6-Me2C6H3
5a
5b
5c
5d
5e
5f
5g
5h
5i
75
88
64
70
78
75
78
88
55
65
69
63
4-ClꢀC6H4
2-ClꢀC6H4
4-MeꢀC6H4
4-BrꢀC6H4
3-BrꢀC6H4
3-NO2ꢀC6H4
3-MeOꢀC6H4
Ph
3i
3b
3h
Ph
5j
5k
5l
4-ClꢀC6H4
3-MeOꢀC6H4
The mass spectrum of 5a shows the molecular-ion peak at m/z 391. The IR spectrum
of 5a exhibits absorption bands due to C¼O groups at 1700 and 1649 cmꢀ1 and two
1
broad absorption bands for the NH groups at 3331 and 3283 cmꢀ1. The H-NMR
spectrum of 5a consists of a m for the cyclohexane CH2 groups (d(H) 0.99 – 1.74), a
NHꢀCH resonance (d(H) 3.35, overlap with solvent), and two d for the two CH groups
(d(H) 3.74 and 4.33, J ¼ 10.4), besides three broad resonances (d(H) 8.03, 10.29, and
10.49) for the NH groups and characteristic signals for the aromatic H-atoms. Due to
the very low solubility of 5a, we were unable to obtain the 13C-NMR spectrum.
The study of the scope and limitations of the described IMCR with respect to the
aldehyde component ArCHO (3) revealed that substituted aromatic aldehydes
containing electron-withdrawing groups and electron-donating groups all tolerate the
reaction conditions giving rise to good yields (Table 1). When the reaction was carried
out with an aliphatic aldehyde such as butanal or propanal, TLC and 1H-NMR spectra

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of the reaction mixture showed a combination of starting materials and numerous
products and the yield of the expected product was very low.
The formation of acetamides 5 can be rationalized by the initial formation of a 1,5-
benzodiazepine 6 via condensation of 1 and 2. Then, Knoevenagel condensation
reaction of 3 and 6 produces intermediate 7. Intermediate 8 is generated by the
Michael-type addition reaction of an isocyanide 4 to 7, and subsequent uptake of H2O
yields 9 which is tautomerized to amide 5 (Scheme 1) [4g].
Scheme 1. Proposed Mechanism of the One-Pot Isocyanide-Based Multicomponent Reaction
Ferrocene derivatives containing heterocyclic systems have attracted special
attention in recent years [22]. Due to the importance of ferrocene-containing
heterocyclic compounds, we also used ferrocenecarboxaldehyde (10) in the above
described reaction. This made it possible to synthesize the new ferrocene-containing
benzodiazepines 11 (Scheme 2).
Scheme 2. Synthesis of Ferrocene-Containing Benzodiazepines of Type 5
Finally, some of the synthesized compounds were screened for antimicrobial
activity. The microorganisms used in this study were Bacillus subtilis ATCC 465 and
Staphylococcus aureus ATCC 25923 (Gram-positive bacteria), Escherichia coli ATCC
25922 and Pseudomonas aeruginusa ATCC 85327 (Gram-negative bacteria), and

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487
Candida albicans ATCC 10231 and Saccharomyses cervisiae ATCC 9763 (fungi). The
minimum inhibitory concentration (MIC) of the synthesized compounds was
determined by the microdilution method [23] (Table 2). As can be seen from Table 2,
good to improved antibacterial activity was observed for most of the compounds
against all species of Gram-positive and Gram-negative bacteria and fungi used in the
study. Compounds 5i and 5b were found to be selectively active against the tested fungi
and Gram-positive bacteria, respectively.
Table 2. MIC Values of Some Products 5 and 11a
MIC [mg/ml]
5a
5b
5c
5f
5h
5i
5j
32
64
64
256
32
128
5k
11a
Bacillus subtilis
Staphylococcus aureus
Escherichia coli
Pseudomonas aeruginosa
Candida albicans
Saccharomyses cervisiae
128
128
16
16
64
64
256
–
–
–
32
16
–
16
32
32
16
16
–
4
16
32
32
–
–
–
–
16
32
8
64
64
16
32
64
64
32
256
–
128
–
–
128
256
128
16
32
–
In conclusion, we developed an efficient one-pot synthesis of a-aryl-2,3,4,5-
tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamides starting from simple and
readily available precursors under neutral conditions without any need of activation or
modifications. The products are of potential synthetic and pharmacological interest.
The simplicity of the presented procedure makes it an interesting alternative to the
complex multistep approaches for the synthesis of 1,5-benzodiazepines.
We gratefully acknowledge financial support from the Research Council of Shahid Beheshti
University.
Experimental Part
General. All chemicals were obtained from Fluka and Merck and used without further purification.
M.p.: Electrothermal-9100 apparatus; uncorrected. IR Spectra (KBr): Bomem-MB FT-IR apparatus; in
cmꢀ1. 1H-NMR Spectra: Bruker-DRX-300-Avance spectrometer; at 300.13 MHz in (D6)DMSO; d in ppm
rel. to Me4Si as internal standard, J in Hz. 13C-NMR Spectra: no data due to the very low solubility of the
products. EI-MS (70 eV): Finningan-MAT-8430 mass spectrometer; in m/z. Elemental analyses:
Heraeus-CHN-O-Rapid analyzer.
Acetamides 5: General Procedure (Table 1). A mixture of benzene-1,2-diamine (1; 1 mmol),
Meldrumꢀs acid (2; 1 mmol), aldehyde 3 (1 mmol), cyclohexyl isocyanide 4 (1 mmol), and H2O (0.5 ml)
in CH2Cl2 (4 ml) was stirred for 36 h at r.t. After completion of the reaction (TLC (AcOEt/hexane 1:1)
monitoring), hexane (3 ml) was added, the mixture filtered, and the precipitate washed with EtOH
(5 ml) to afford the pure product.
N-Cyclohexyl-2,3,4,5-tetrahydro-2,4-dioxo-a-phenyl-1H-1,5-benzodiazepine-3-acetamide (5a): Yield
75%. White powder. M.p. > 2608. IR: 3331, 3283, 3065 (NH), 1700, 1649, 1606 (C¼O). 1H-NMR: 0.99 –
1.74 (m, 5 CH2 of Chx); 3.35 (br. s, CH of Chx, overlap with solvent); 3.74 (d, J ¼ 10.4, CH); 4.33 (d, J ¼
10.4, CH); 7.11 – 7.39 (m, 9 arom. H); 8.03 (br. s, NHꢀChx); 10.29 (s, NH); 10.49 (s, NH). EI-MS: 391
(Mþ). Anal. calc. for C23H25N3O3 (391.46): C 70.57, H 6.44, N 10.73; found: C 70.48, H 6.38, N 10.65.
a-(4-Chlorophenyl)-N-cyclohexyl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5b): Yield 88%. White powder. M.p. > 2608. IR: 3319, 3216, 3074 (NH), 1699, 1646, 1602(C¼O).
1H-NMR: 0.98 – 1.65 (m, 5 CH2 of Chx); 3.36 (br. s, CH of Chx, overlap with solvent); 3.71 (d, J ¼ 11.3,

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CH); 4.35 (d, J ¼ 11.3, CH); 7.10 – 7.42 (m, 8 arom. H); 8.08 (d, J ¼ 7.1, NHꢀChx); 10.34 (s, NH); 10.53 (s,
NH). EI-MS: 425 (Mþ). Anal. calc. for C23H24ClN3O3 (425.91): C 64.86, H 5.68, N 9.87; found: C 64.74, H
5.59, N 9.96.
a-(2-Chlorophenyl)-N-cyclohexyl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5c): Yield 64%. White powder. M.p. > 2608. IR: 3346, 3265, 3080 (NH), 1701, 1651, 1605 (C¼O).
1H-NMR: 1.08 – 1.69 (m, 5 CH2 of Chx); 3.47 (br. s, CH of Chx, overlap with solvent); 3.95 (d, J ¼ 11.2,
CH); 4.72 (d, J ¼ 11.2, CH); 7.14 – 7.37 (m, 8 arom. H); 7.57 (d, J ¼ 8.1, NHꢀChx); 10.31 (s, NH); 10.62 (s,
NH). EI-MS: 425 (Mþ). Anal. calc. for C23H24ClN3O3 (425.91): C 64.86, H 5.68, N 9.87; found: C 64.94, H
5.48, N 9.80.
N-Cyclohexyl-2,3,4,5-tetrahydro-a-(4-methylphenyl)-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5d): Yield 70%. White powder. M.p. > 2608. IR: 3324, 3214, 3075 (NH), 1699, 1647, 1603 (C¼O).
1H-NMR: 0.94 – 1.65 (m, 5 CH2 of Chx); 2.20 (s, Me); 3.36 (br. s, CH of Chx, overlap with solvent); 3.69
(d, J ¼ 11.3, CH); 4.28 (d, J ¼ 11.2, CH); 6.97 – 7.27 (m, 8 arom. H); 7.99 (d, J ¼ 7.8, NHꢀChx); 10.26 (s,
NH); 10.48 (s, NH). EI-MS: 405 (Mþ). Anal. calc. for C24H27N3O3 (405.49): C 71.09, H 6.71, N 10.36;
found: C 70.99, H 6.79, N 10.45.
a-(4-Bromophenyl)-N-cyclohexyl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5e): Yield 78%. White powder. M.p. > 2708. IR: 3315, 3214, 3071 (NH), 1699, 1647, 1603 (C¼O).
1H-NMR: 0.99 – 1.66 (m, 5 CH2 of Chx); 3.33 (br. s, CH of Chx, overlap with solvent); 3.73 (d, J ¼ 8.8,
CH); 4.35 (d, J ¼ 8.8, CH); 6.95 – 7.49 (m, 8 arom. H); 8.03 (br. s, NHꢀChx); 10.28 (s, NH); 10.47 (s, NH).
EI-MS: 471 (Mþ), 469 (Mþ). Anal. calc. for C23H24BrN3O3 (470.36): C 58.73, H 5.14, N 8.93; found: C
58.81, H 5.21, N 8.82.
a-(3-Bromophenyl)-N-cyclohexyl-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5f): Yield 75%. White powder. M.p. > 2708. IR: 3317, 3185, 3069 (NH), 1700, 1648, 1601 (C¼O).
1H-NMR: 1.14 – 1.65 (m, 5 CH2 of Chx); 3.38 (br. s, CH of Chx, overlap with solvent); 3.71 (d, J ¼ 9.6,
CH); 4.32 (d, J ¼ 9.6, CH); 7.20 – 7.48 (m, 8 arom. H); 8.10 (br. s, NHꢀChx); 10.37 (s, NH); 10.55 (s, NH).
EI-MS: 471 (Mþ), 469 (Mþ). Anal. calc. for C23H24BrN3O3 (470.36): C 58.73, H 5.14, N 8.93; found: C
58.60, H 5.07, N 8.81.
N-Cyclohexyl-2,3,4,5-tetrahydro-a-(3-nitrophenyl)-2,4-dioxo-1H-1,5-benzodiazepine-3-acetamide
(5g): Yield 78%. White powder. M.p. > 2608. IR: 3316, 3216, 3069 (NH), 1700, 1646, 1605 (C¼O).
1H-NMR: 0.94 – 1.76 (m, 5 CH2 of Chx); 3.36 (br. s, CH of Chx, overlap with solvent); 3.79 (d, J ¼ 11.3,
CH); 4.52 (d, J ¼ 11.3, CH); 7.08 – 8.21 (m, 7 arom. H); 8.05 (d, J ¼ 8, NHꢀChx); 8.18 – 8.21 (m, 2 arom.
H); 10.38 (s, NH); 10.60 (s, NH). EI-MS: 436 (Mþ). Anal. calc. for C23H24N4O5 (436.46): C 63.29, H 5.54,
N 12.84; found: C 63.36, H 5.62, N 12.75.
N-Cyclohexyl-2,3,4,5-tetrahydro-a-(3-methoxyphenyl)-2,4-dioxo-1H-1,5-benzodiazepine-3-acet-
amide (5h): Yield 88%. White powder. M.p. > 2608. IR: 3361, 3260, 3060 (NH), 1690, 1677, 1605 (C¼O).
1H-NMR: 1.15 – 1.65 (m, 5 CH2 of Chx); 3.38 (br. s, CH of Chx, overlap with solvent); 3.67 (br. s, MeO,
CH); 4.29 (br. s, CH); 6.77 – 7.21 (m, 8 arom. H); 8.03 (br. s, NHꢀChx); 10.30 (s, NH); 10.49 (s, NH). EI-
MS: 421 (Mþ). Anal. calc. for C24H27N3O4 (421.49): C 68.39, H 6.46, N 9.97; found: C 68.28, H 6.38, N
10.09.
2,3,4,5-Tetrahydro-N-{[(4-methylphenyl)sulfonyl]methyl}-2,4-dioxo-a-phenyl-1H-1,5-benzodiaze-
pine-3-acetamide (5i): Yield 55%. White powder. M.p. 228 – 2328. IR: 3555, 3300, 3266 (NH), 1687, 1630,
1601 (C¼O). 1H-NMR: 2.34 (s, Me); 4.29 – 4.71 (m, 2 CH, CH2); 6.41 – 7.32 (m, 13 arom. H, NH); 8.95
(br. s, NH); 9.18 (br. s, NH). EI-MS: 477 (Mþ). Anal. calc. for C25H23N3O5S (477.53): C 62.88, H 4.85, N
8.80; found: C 62.74, H 4.73, N 8.71.
N-(2,6-Dimethylphenyl)-2,3,4,5-tetrahydro-2,4-dioxo-a-phenyl-1H-1,5-benzodiazepine-3-acetamide
(5j): Yield 64%. White powder. M.p. > 2608. IR: 3450, 3256, 3064 (NH), 1702, 1656, 1601 (C¼O).
1H-NMR: 1.88 (s, 2 Me); 3.84 (d, J ¼ 10.8, CH); 4.64 (d, J ¼ 10.8, CH); 6.96 – 7.55 (m, 12 arom. H); 9.40 (s,
NH); 10.16 (s, NH); 10.63 (s, NH). EI-MS: 413 (Mþ). Anal. calc. for C25H23N3O3 (413.47): C 72.62, H
5.61, N 10.16; found: C 72.79, H 5.55, N 10.23.
a-(4-Chlorophenyl)-N-(2,6-dimethylphenyl)-2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepine-3-
acetamide (5k): Yield 69%. White powder. M.p. > 2608. IR: 3450, 3300, 3290 (NH), 1699, 1662, 1600
(C¼O). 1H-NMR: 1.94 (s, 2 Me); 3.81 (d, J ¼ 12.9, CH); 4.65 (d, J ¼ 12.9, CH); 6.97 – 7.54 (m, 11 arom.

Helvetica Chimica Acta – Vol. 95 (2012)
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H); 9.65 (s, NH); 10.39 (s, NH); 10.67 (s, NH). EI-MS: 447 (Mþ). Anal. calc. for C25H22ClN3O3 (447.91):
C 67.04, H 4.95, N 9.38; found: C 67.14, H 4.87, N 9.31.
N-(2,6-Dimethylphenyl)-2,3,4,5-tetrahydro-a-(3-methoxyphenyl)-2,4-dioxo-1H-1,5-benzodiazepine-
3-acetamide (5l): Yield 63%. White powder. M.p. > 2608. IR: 3291, 3228, 3078 (NH), 1700, 1656 (C¼O).
1H-NMR: 1.92 (s, 2 Me); 3.77 (s, MeO); 3.85 (d, J ¼ 11.2, CH); 4.62 (d, J ¼ 11.2, CH); 6.76 – 7.20 (m, 11
arom. H); 9.40 (s, NH); 10.17 (s, NH); 10.42 (s, NH). EI-MS: 443 (Mþ). Anal. calc. for C26H25N3O4
(443.49): C 70.41, H 5.68, N 9.47; found: C 70.30, H 5.61; N 9.55.
[2-(Cyclohexylamino)-2-oxo-1-(2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepin-3-yl)ethyl]ferro-
cene (11a): Yield 67%. Light yellow solid. M.p. > 2608. IR: 3460, 3300, 3074 (NH), 1700, 1655, 1603
1
(C¼O). H-NMR: 1.19 – 1.83 (m, 5 CH2 of Chx); 3.56 (br. s, CH of Chx); 3.94 – 4.18 (m, CHfer, 2 CH);
7.08 – 7.18 (m, 4 arom. H); 8.10 (d, J ¼ 7.6, NHꢀChx); 10.38 (s, NH); 10.40 (s, NH). EI-MS: 499 (Mþ).
Anal. calc. for C27H29FeN3O3: C 64.94, H 5.85, N 8.41; found: C 64.81, H 5.76, N 8.49.
{2-[(2,6-Dimethylphenyl)amino]-2-oxo-1-(2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepin-3-
yl)ethyl}ferrocene (11b): Yield 58%. White powder. M.p. 228 – 2358. IR: 3450, 3300, 3261 (NH), 1680,
1662, 1600 (C¼O). 1H-NMR: 2.19 (s, 2 Me); 4.22 – 4.80 (m, CHfer, 2 CH); 6.53 – 7.31 (m, 7 arom. H); 9.09
(s, NH); 9.20 (s, NH); 9.65 (s, NH). EI-MS: 521 (Mþ). Anal. calc. for C29H27FeN3O3: C 66.80, H 5.22, N
8.06; found: C 66.89, H 5.28, N 7.99.
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