Catalyst-free synthesis of α-aminoacylamides via n,n'- bis(phenylmethylidene) phenylmethanediamine as imine surrogate in ugi multicomponent reaction

Article abstract of DOI:10.1080/00397911.2010.529229

A novel one-pot, multicomponent, and catalyst-free reaction of N,N'-bis (phenylmethylidene) phenylmethane, carboxylic acids, and isocyanides yielding α-aminoacyl-amides is described. The reaction is based on the combination of an Ugi three-component reaction followed by hydrolysis. Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397911.2010.529229

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Catalyst-Free Synthesis of α-
Aminoacyl-amides via N,N′-
Bis(Phenylmethylidene)phenylmethanediami
as Imine Surrogate in Ugi
Multicomponent Reaction
Abdolali Alizadeh a & Javad Mokhtari a
a Department of Chemistry, Tarbiat Modares University, Tehran, Iran
Accepted author version posted online: 17 Aug 2011.
To cite this article: Abdolali Alizadeh & Javad Mokhtari (2012) Catalyst-Free Synthesis of α-
Aminoacyl-amides via N,N′-Bis(Phenylmethylidene)phenylmethanediamine as Imine Surrogate
in Ugi Multicomponent Reaction, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 42:5, 686-693, DOI: 10.1080/00397911.2010.529229
To link to this article: http://dx.doi.org/10.1080/00397911.2010.529229
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Synthetic Communications1, 42: 686–693, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2010.529229
CATALYST-FREE SYNTHESIS OF a-AMINOACYL-
AMIDES VIA N,N’-BIS(PHENYLMETHYLIDENE)
PHENYLMETHANEDIAMINE AS IMINE SURROGATE
IN UGI MULTICOMPONENT REACTION
Abdolali Alizadeh and Javad Mokhtari
Department of Chemistry, Tarbiat Modares University, Tehran, Iran
GRAPHICAL ABSTRACT
Abstract A novel one-pot, multicomponent, and catalyst-free reaction of N,N’-bis (phenyl-
methylidene)phenylmethane, carboxylic acids, and isocyanides yielding a-aminoacyl-amides
is described. The reaction is based on the combination of an Ugi three-component reaction
followed by hydrolysis.
Keywords Diimine; isocyanide; three-component reaction; Ugi reaction
INTRODUCTION
Multicomponent reactions (MCRs) have recently become one of the favored
methods to prepare pharmacologically relevant compounds.[1] Among many kinds
of multicomponent condensations, the Ugi reaction,[2] discovered more than 40 years
ago, is without any doubt the most widely exploited, not only to prepare peptide-like
molecules but also to achieve many different types of biologically active targets.[3]
The large range of structures accessible through this powerful reaction is continually
expanding, through ongoing development of variations of the MCR, together with
an increasing number of elaborate post-condensation modifications and cascade
processes.[4–6] Despite such widespread application, use of diimines as readily avail-
able nitrogen source in the Ugi three-component condensation (3-CC) has received
comparatively little attention. Diimines serve as a good precursor for the synthesis of
numerous organic compounds, especially aza-cyclic compounds.[7–12] This easily
accessible precursor can be produced by the reaction of aromatic aldehydes and
ammonia solution. As part of our continuing effort to design new routes for the
Received August 16, 2010.
Address correspondence to Abdolali Alizadeh, Department of Chemistry, Tarbiat Modares
University, P. O. Box 14115-175, Tehran, Iran. E-mail: aalizadeh@modares.ac.ir
686

UGI-MULTICOMPONENT REACTION
687
Table 1. Reaction of N,N0-bis(phenylmethylidene)phenylmethanediamine, carboxylic acids 1, and isocya-
nides 2
3
R
R0
t-Bu
Yield of 3 (%)
a
b
c
d
e
f
Bn
Bn
98
94
95
93
92
96
95
94
96
98
Cyclohexyl
t-Bu
Ph2CH-
Ph2CH-
Cyclohexyl
t-Bu
Cinammyl
Cinammyl
P-NO2C6H4
P-NO2C6H4
Furyl
Cyclohexyl
t-Bu
g
h
i
Cyclohexyl
t-Bu
Cyclohexyl
j
Furyl
preparation of biologically active compounds,[13–16] herein we describe a simple,
one-pot, three-component synthesis of a-aminoacyl-amides derivatives. The reaction
of N,N0-bis(phenylmethylidene)phenylmethanediamine and carboxylic acid 1 in the
presence of isocyanides 2 in anhydrous toluene at reflux condition produces title
compound 3 in 92–98% yields (Table 1).
RESULTS AND DISCUSSION
Regarding the well-documented general mechanism of the Ugi reaction,[2,5] we
proposed a five-key-step plausible mechanism for the mentioned reaction (Scheme 1).
The first step begins through a protonation of N,N0-bis(phenylmethylidene)phenyl-
methanediamine to produce iminium salt 4. Then isocyanide 2 is subsequently added
to the iminium salt 4 to produce the reactive nitrilium intermediate 5. The reactive O-
acyl iminolate 6 is formed via the a-addition of the carboxylate anion to the nitrilium
ion 5. Another step involves O- to N-acyl transfer (Mumm rearrangement) to afford
the intermediate 7. Finally, intermediate 7 in the presence of air, moisture, or water is
converted to product 3. To our delight, we found that the desired product could be
isolated in all cases with good to quantitative yields.
The structures of compounds 3a–j were deduced from their elemental analysis,
1
infrared (IR), and high-field H and 13C NMR spectra.

688
A. ALIZADEH AND J. MOKHTARI
Scheme 1. Proposed mechanism for the formation of a-aminoacyl-amide.
CONCLUSION
In summary, we have demonstrated that the one-pot, three-component Ugi
reaction of diimine, carboxcylic acides, and isocyanide provides a simple method
for the preparation of a-aminoacyl-amides of potential synthetic. Fairly good yields
of the products without any activation, the ready availability of the starting materi-
als, the reaction’s simplicity, and its mild conditions are the main advantages of this
method.
EXPERIMENTAL
All chemicals were obtained from Merck (Germany) and Fluka (Switzerland).
1H and 13C NMR spectra were measured (CDCl3 solution) with a Bruker DRX-500
Avance spectrometer at 500.13 and 125.75 MHz, respectively. IR spectra were
recorded on a Shimadzu IR-460 spectrometer. Chromatography columns were pre-
pared from Merck silica gel, 230–240 mesh. Mass spectra were obtained using a
Finnigan-Mat 8430 spectrometer operating at an ionization potential of 70 eV.
Typical Procedure for Preparation of N’-(tert-Butyl)-2-phenyl-2-
[(2-phenylacetyl)amino]acetamide (3a)
To a magnetically stirred solution of NH4OH (30%, 5 mL), 0.16 g benzal-
dehyde (1.5 mmol) was added, and the solution was stirred for 5 h at reflux. During
this time, a white precipitate formed. The precipitate was removed by filtration and
dried. The solid was dissolved in toluene (5 mL), and 0.14 g 2-phenylacetic acid

UGI-MULTICOMPONENT REACTION
689
(1 mmol) and 0.08 g tert-butyl isocyanide (1 mmol) were added to the mixture. The
resulting solution was stirred for 12 h at reflux. When the reaction mixture was
cooled to room temperature, a white solid precipitated. The precipitates were filtered
and washed with diethyl ether to give product 3a in 98% yields. All products gave
satisfactory spectral data in accordance with the assigned structures (0.32 g, 98%).
N1-(tert-Butyl)-2-phenyl-2-[(2-phenylacetyl)amino]acetamide (3a)
Yield: 0.32 g (98%); whiteꢁ1crystals; mp ¼ 184–186 ꢀC. IR (KBr): 3287 (NH),
1
=
1636 (C O), 1558 and 1494 cm (Ar). H NMR (500.13 MHz, CDCl3): dH ¼ 1.24
3
(9 H, s, Me3C), 3.57 (2 H, s, CH2), 5.38 (1 H, d, JHH ¼ 7.0 Hz, CH), 5.69 (1 H, s,
3
NH), 6.92 (1 H, d, JHH ¼ 6.4 Hz, NH), 7.23–7.34 ppm (10 H, m, 10 CH of Ar).
13C NMR (125.75 MHz, CDCl3): dC ¼ 28.53 (Me3C), 43.60 (CH2), 51.74 (Me3C),
57.34 (CH), 127.11 (2 CH of Ar), 127.24 (CH of Ar), 128.13 (CH of Ar), 128.87
(2 CH of Ar), 128.90 (2 CH of Ar), 129.29 (2 CH of Ar), 134.67 (Cipso-CH2),
=
=
138.54 (Cipso-CH), 168.83 (C O), 170.25 ppm (C O). MS (EI, 70 eV): m=z
(%) ¼ 324 (Mþ, 4), 224 (35), 210 (42), 105 (73), 91 (50), 71 (65), 57 (100), 43 (92).
Anal. calcd. for C20H24N2O2 (324.42): C, 74.05; H, 7.46; N, 8.63%. Found: C,
74.07; H, 7.47; N, 8.64%.
N1-Cyclohexyl-2-phenyl-2-[(2-phenylacetyl)amino]acetamide (3b)
Yield: 0.33 g (94%); white crystals; mp ¼ 244–246 ꢀC. IR (KBr): 3305 (NH),
ꢁ1
1
1681 and 1631 (C O), 1525 and 1493 cm (Ar). H NMR (500.13 MHz, CDCl3):
=
dH ¼ 0.84–1.86 (10 H, m, 5 CH2 of cyclohexyl), 3.58 (2 H, s, CH2), 3.72 (1 H, m,
3
3
CH), 5.33 (1 H, d, JHH ¼ 6.8 Hz, CH), 5.37 (1 H, d, JHH ¼ 7.3 Hz, NH), 6.84 (1
H, d, JHH ¼ 5.7 Hz, NH), 7.25–7.39 ppm (10 H, m, 10 CH of Ar). 13C NMR
3
(125.75 MHz, CDCl3): dC ¼ 24.53 (CH2), 24.67 (CH2), 25.36 (CH2), 32.58 (CH2),
32.77 (CH2), 41.67 (CH2), 48.72 (CH), 57.18 (CH), 125.3 (2 CH of Ar), 127.22
(CH of Ar), 127.32 (CH of Ar), 128.94 (2 CH of Ar), 128.97 (2 CH of Ar), 129.34
=
(2 CH of Ar), 134.60 (Cipso-CH2), 138.31 (Cipso-CH), 168.65 (C O), 170.28 ppm
þ
=
(C O). MS (EI, 70 eV): m=z (%) ¼ 350 (M , 1), 259 (1), 225 (100), 188 (5), 106
(74), 91 (80), 77 (8), 55 (18), 41 (12). Anal. calcd. for C22H26N2O2 (350.46): C,
75.40; H, 4.48; N, 7.99%. Found: C, 75.48; H, 4.52; N, 8.01%.
N1-(tert-Butyl)-2-[(2,2-diphenylacetyl)amino]-2-phenylacetamide (3c)
Yield: 0.38 g (95%); whiteꢁ1crystals; mp ¼ 246–248 ꢀC. IR (KBr): 3290 (NH),
1
=
1636 (C O), 1547 and 1491 cm (Ar). H NMR (500.13 MHz, CDCl3): dH ¼ 1.21
3
(9 H, s, Me3C), 4.95 (1 H, s, CH), 5.40 (1 H, d, JHH ¼ 6.8 Hz, CH), 5.65 (1 H, s,
3
NH), 7.05 (1 H, d, JHH ¼ 7.4 Hz, NH), 7.18–7.30 ppm (15 H, m, 15 CH of Ar).
13C NMR (125.75 MHz, CDCl3): dC ¼ 28.50 (Me3C), 51.74 (Me3C), 57.64 (CH),
58.78 (CH), 127.16 (2 CH of Ar), 127.19 (CH of Ar), 127.22 (CH of Ar), 128.15
(CH of Ar), 128.68 (2 CH of Ar), 128.80 (2 CH of Ar), 128.88 (2 CH of Ar),
128.94 (2 CH of Ar), 129.24 (2 CH of Ar), 138.36 (Cipso-CH), 139.18 (Cipso-CH),
=
=
139.24 (Cipso-CH), 168.72 (C O), 171.27 ppm (C O). MS (EI, 70 eV): m=z
(%) ¼ 401 (Mþ þ 1, 1), 301 (58), 233 (23), 167 (100), 152 (16), 134 (27), 106 (53),

690
A. ALIZADEH AND J. MOKHTARI
91 (8), 57 (22), 41 (9). Anal. calcd. for C26H28N2O2 (400.52): C, 77.97; H, 7.05; N,
6.99%. Found: C, 77.98; H, 7.07; N, 6.99%.
N1-Cyclohexyl-2-[(2,2-diphenylacetyl)amino]-2-phenylacetamide (3d)
Yield: 0.4 g (93%); white crystals; mp ¼ 220–222 ꢀC. IR (KBr): 3285 (NH), 1632
(C O), 1542 and 1491 cmꢁ1 (Ar). 1H NMR (500.13 MHz, CDCl3): dH ¼ 0.86–1.80 (10
=
H, m, 5 CH2 of cyclohexyl), 3.66 (1 H, m, CH), 4.96 (1 H, s, CH), 5.45 (1 H, d,
3
3JHH ¼ 6.7 Hz, CH), 5.64 (1 H, br, NH), 7.06 (1 H, d, JHH ¼ 6.65 Hz, NH),
7.21–7.35 ppm (15 H, m, 15 CH of Ar). 13C NMR (125 MHz, CDCl3): dC ¼ 24.54
(CH2), 24.69 (CH2), 25.35 (CH2), 32.52 (CH2), 32.69 (CH2), 48.69 (CH of cyclohexyl),
57.37 (CH), 58.86 (CH), 127.23 (4 CH of Ar), 128.26 (CH of Ar), 128.67 (2 CH of Ar),
128.71 (2 CH of Ar), 128.83 (2 CH of Ar), 128.92 (4 CH of Ar), 138.24 (Cipso-CH),
=
=
139.16 (Cipso-CH), 139.24 (Cipso-CH), 168.59 (C O), 171.29 ppm (C O). MS (EI,
70 eV): m=z (%) ¼ 427 (Mþ þ 1, 1), 301 (66), 259 (53), 188 (32), 167 (100), 152 (16),
106 (57), 55 (18), 41 (9). Anal. calcd. for C28H30N2O2 (426.56): C, 78.84; H, 7.09;
N, 6.57%. Found: C, 59.98; H, 7.82; N, 4.81%.
(E)-N1-[2-(tert-Butylamino)-2-oxo-1-phenylethyl]-3-phenyl-2-
propenamide (3e)
Yield: 0.31 g (92%); white crystals; mp ¼ 234–236 ꢀC. IR (KBr): 3290 (NH),
ꢁ1
1
1643 and 1618 (C O), 1547 and 1495 cm (Ar). H NMR (500.13 MHz, CDCl3):
=
3
dH ¼ 1.31 (9 H, s, Me3C), 5.58 (1 H, d, JHH ¼ 8.4 Hz, CH), 5.79 (1 H, s, NH), 6.49
3
3
(1 H, d, JHH ¼ 15.7 Hz, CH), 7.21 (1 H, d, JHH ¼ 7.4 Hz, NH), 7.26–7.47 (10 H,
m, 10 CH of Ar), 7.59 ppm (1 H, d, JHH ¼ 15.7 Hz, CH). 13C NMR (125.75 MHz,
3
CDCl3): dC ¼ 28.60 (Me3C), 51.89 (Me3C), 57.37 (CH), 120.53 (CH¼CHCO),
127.31 (2 CH of Ar), 127.84 (2 CH of Ar), 128.22 (CH of Ar), 128.81 (2 CH of
-
=
Ar), 128.99 (2 CH of Ar), 129.72 (CH of Ar), 134.81 (Cipso-C C), 138.64 (Cipso
=
=
=
CH), 141.43 (CH CHCO), 165.15 (C O), 169.15 ppm (C O). MS (EI, 70 eV): m=z
(%) ¼ 337 (Mþ þ 1, 1), 237 (85), 193 (5), 131 (100), 103 (38), 90 (2), 77 (22), 57 (14),
41 (7). Anal. calcd. for C21H24N2O2(336.43): C, 74.97; H, 7.19; N, 8.33%. Found:
C, 74.9; H, 7.25; N, 8.38%.
(E)-N1-[2-(Cyclohexylamino)-2-oxo-1-phenylethyl]-3-phenyl-
2-propenamide (3f)
Yield: 0.35 g (96%); white crystals; mp ¼ 251–252 ꢀC. IR (KBr): 3277 (NH),
ꢁ1
1
=
1643 and 1615 (C O), 1547 and 1449 cm (Ar). H NMR (500.13 MHz, CDCl3):
dH ¼ 1.03–1.93 (10 H, m, 5 CH2 of cyclohexyl), 3.76–3.78 (1 H, m, CH), 5.57 (1 H,
d, 3JHH ¼ 6.9 Hz, CH), 5.68 (1 H, d, 3JHH ¼ 7.7 Hz, NH), 6.5 (1 H, d, 3JHH ¼ 15.6 Hz,
3
Hz, CH), 7.15 (1 H, d, JHH ¼ 6.5 Hz, NH), 7.26–7.49 (10 H, m, 10 CH of Ar),
7.60 ppm (1 H, d, JHH ¼ 15.6 Hz, CH). 13C NMR (125 MHz, CDCl3): dC ¼ 24.59
3
(CH2), 24.70 (CH2), 25.41 (CH2), 32.65 (CH2), 32.83 (CH2), 48.82 (CH), 57.24
(CH), 120.39 (CH¼CHCO), 127.37 (2 CH of Ar), 127.86 (2 CH of Ar), 128.32
(CH of Ar), 128.82 (2 CH of Ar), 129.02 (2 CH of Ar), 129.75 (CH of Ar), 134.79
=
(Cipso-C C), 138.43 (Cipso-CH), 141.58 (CH CHCO), 165.18 (C O), 168.94 ppm
=
=

UGI-MULTICOMPONENT REACTION
691
þ
=
(C O). MS (EI, 70 eV): m=z (%) ¼ 363 (M þ 1, 2), 237 (100), 193 (4), 131 (97), 103
(33), 77 (17), 55 (11). Anal. calcd. for C23H26N2O2(362.47): C, 76.21; H, 7.23; N,
7.73%. Found: C, 76.22; H, 7.25; N, 7.72%.
N1-[2-(tert-Butylamino)-2-oxo-1-phenylethyl]-4-nitrobenzamide (3g)
Yield: 0.34 g (95%); white crystals; mp ¼ 260–262 ꢀC. IR (KBr): 3325 (NH),
ꢁ1
1
1671 and 1636 (C O), 1547 and 1522 cm (Ar). H NMR (500.13 MHz, CDCl3):
=
3
dH ¼ 1.31 (9 H, s, Me3C), 5.49 (1 H, s, NH), 5.50 (1 H, q, JHH ¼ 3.4 Hz, CH),
3
7.26–7.40 (3 H, m, CH of Ar), 7.46 (2 H, d, JHH ¼ 8.5 Hz, CH of Ar), 7.85 (1 H,
3
3
br, NH), 7.98 (2 H, d, JHH ¼ 8.8 Hz, CH of Ar), 8.26 ppm (2 H, d, JHH ¼ 8.8 Hz,
CH of Ar). 13C NMR (125.75 MHz, CDCl3): dC ¼ 28.55 (Me3C), 52.16 (Me3C),
57.77 (CH), 123.72 (2 CH of Ar), 127.41 (2 CH of Ar), 128.37 (2 CH of Ar),
=
128.63 (CH of Ar), 129.22 (2 CH of Ar), 138.17 (Cipso-CH), 139.50 (Cipso-C O),
=
=
149.75 (Cipso-NO2), 164.34 (C O), 168.62 ppm (C O). MS (EI, 70 eV): m=z
(%) ¼ 313 (2), 256 (100), 239 (6), 209 (8), 150 (89), 120 (12), 104 (53), 76 (25), 57
(41), 41 (19). Anal. calcd. for C19H21N3O4 (355.39): C, 64.21; H, 5.96; N, 11.82%.
Found: C, 64.22; H, 5.97; N, 11.83%.
N1-[2-(Cyclohexylamino)-2-oxo-1-phenylethyl]-4-nitrobenzamide (3h)
Yield: 0.36 g (94%); white crystals; mp ¼ 200–202 ꢀC. IR (KBr): 3282 (NH),
ꢁ1
1
=
1632 (C O), 1543 and 1516 cm (Ar). H NMR (500.13 MHz, CDCl3): dH ¼ 1.07–
1.77 (m, 10 H, 5 CH2 of cyclohexyl), 3.52–3.54 (1 H, m, CH), 5.69 (1 H, d,
3JHH ¼ 8.1 Hz, CH), 7.27 (1 H, d, JHH ¼ 7.2 Hz, NH), 7.34 (2 H, d, JHH ¼ 7.6 Hz,
3
3
3
3
2 CH of Ar), 7.50 (2 H, d, JHH ¼ 7.5 Hz, 2 CH of Ar), 8.13 (2 H, t, JHH ¼ 8.6 Hz,
3
3
2 CH of Ar), 8.23 (1 H, t, JHH ¼ 7.2 Hz, CH of Ar), 8.27 (2 H, d, JHH ¼ 8.6 Hz, 2
CH of Ar), 9.23 ppm (1 H, d, 3JHH ¼ 8.0 Hz, NH). 13C NMR (125.75 MHz, CDCl3):
dC ¼ 24.33 (CH2), 24.44 (CH2), 25.13 (CH2), 32.12 (CH2), 32.20 (CH2), 47.75 (CH),
57.02 (CH), 123.27 (2 CH of Ar), 127.51 (CH of Ar), 128.23 (2 CH of Ar), 129.28
=
(2 CH of Ar), 130.23 (2 CH of Ar), 138.48 (Cipso-CH), 139.67 (Cipso-C O), 149.04
=
=
(Cipso-NO2), 164.61 (C O), 168.38 ppm (C O). MS (EI, 70 eV): m=z (%) ¼ 382
(Mþ þ 1, 1), 314 (4), 256 (100), 208 (5), 150 (34), 120 (8), 104 (20), 76 (13), 55 (10),
41 (5). Anal. calcd. for C21H23N3O4 (381.43): C, 66.13; H, 6.08; N, 11.02%. Found:
C, 66.14; H, 6.09; N, 11.04%.
N1-[2-(tert-Butylamino)-2-oxo-1-phenylethyl]-2-furamide (3i)
Yield: 0.29 g (96%); whiteꢁc1rystals; mp ¼ 174–176 ꢀC. IR (KBr): 3334 (NH),
1
=
1640 (C O), 1553 and 1475 cm (Ar). H NMR (500.13 MHz, DMSO-d6): dH ¼
3
1.20 (9 H, s, Me3C), 5.61 (1 H, d, JHH ¼ 8.2 Hz, CH), 6.39 (1 H, s, NH), 6.62 (1 H,
3
3
d, JHH ¼ 5.5 Hz, CH of furyl), 7.26 (1 H, t, JHH ¼ 7.3 Hz, CH of Ar), 7.32 (2 H, t,
3JHH ¼ 7.6 Hz, 2 CH of Ar), 7.42 (2 H, d, JHH ¼ 7.5 Hz, 2 CH of Ar), 7.52 (1 H, s,
3
CH of furyl), 7.84 (1 H, s, CH of furyl), 8.25 ppm (1 H, d, JHH ¼ 7.6 Hz, NH). 13C
3
NMR (125.75 MHz, CDCl3): dC ¼ 28.26 (Me3C), 50.46 (Me3C), 55.7 (CH), 110.69
(CH of furyl), 114.12 (CH of furyl), 126.87 (2 CH of Ar), 127.4 (CH of Ar), 128.24
=
(2 CH of Ar), 139.07 (Cipso-CH), 142.62 (Cipso-C O), 145.35 (CH of furyl), 156.74

692
A. ALIZADEH AND J. MOKHTARI
=
=
(C O), 168.68 ppm (C O). MS (EI, 70 eV): m=z (%) ¼ 236 (15), 450 (23), 183 (10),
112 (21), 95 (68), 71 (65), 57 (100), 43 (97). Anal. calcd. for C17H20N2O3 (300.35):
C, 67.98; H, 6.71; N, 9.33%. Found: C, 67.99; H, 6.72; N, 9.34%.
N2-[2-(Cyclohexylamino)-2-oxo-1-phenylethyl]-2-furamide (3j)
Yield: 0.32 g (98%); white crystals; mp ¼ 154–156 ꢀC. IR (KBr): 3260 (NH),
ꢁ1
1
1671 and 1631 (C O), 1553 and 1473 cm (Ar). H NMR (500.13 MHz, CDCl3):
=
dH ¼ 1.10–1.89 (10 H, m, 5 CH2 of cyclohexyl), 3.75–3.77 (1 H, m, CH), 5.54
3
3
(1 H, d, JHH ¼ 6.6 Hz, CH), 6.00 (1 H, br, NH), 6.47 (1 H, dd, JHH ¼ 3.2 Hz,
3JHH ¼ 1.6 Hz, CH of furyl), 7.07 (1 H, d, JHH ¼ 3.4 Hz, CH of furyl), 7.29–7.34
3
3
(3 H, m, 3 CH of Ar), 7.45 (2 H, d, JHH ¼ 8.7 Hz, 2 CH of Ar), 7.46 (1 H, d,
3JHH ¼ 8.7 Hz, CH of furyl), 7.74 ppm (1 H, d, JHH ¼ 6.4 Hz, NH). 13C NMR
3
(125.75 MHz, CDCl3): dC ¼ 24.61 (CH2), 24.72 (CH2), 25.43 (CH2), 32.63 (CH2),
32.82 (CH2), 48.83 (CH), 56.77 (CH), 112.04 (CH of furyl), 114.58 (CH of furyl),
127.40 (2 CH of Ar), 128.37 (CH of Ar), 129.02 (2 CH of Ar), 138.26 (Cipso-CH),
=
=
=
144.23 (CH of furyl), 147.68 (Cipso-C O), 157.66 (C O), 168.64 ppm (C O). MS
(EI, 70 eV): m=z (%) ¼ 313 (19), 285 (10), 264 (18), 236 (24), 201 (9), 95 (47), 71
(56), 57 (93), 43 (100). Anal. calcd. for C19H22N2O3 (326.34): C, 69.92; H, 6.79; N,
8.58%. Found: C, 69.94; H, 6.80; N, 8.59%.
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