Efficient one-pot synthesis of 4-aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b] pyridin-2-one and 4-aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-one derivatives under solvent-free conditions

Article abstract of DOI:10.1080/00397910802463878

4-Aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]pyridin-2-one and 4-aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-one have been prepared from indan-1-one or 3,4-dihydronaphthalen-1(2H)-one, aromatic aldehydes, 2-cyanoacetamide, in the presence of sodium hy

Full text of DOI:10.1080/00397910802463878

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Efficient One-Pot Synthesis of
4-Aryl-3-cyano-2,5-dihydro-1H-
indeno[1,2-b]pyridin-2-one
and 4-Aryl-3-cyano-1,2,5,6-
tetrahydrobenzo[h]quinolin-2-
one Derivatives Under Solvent-
Free Conditions
Liangce Rong a b , HongXia Han a , Hong Jiang b ,
Qiya Zhang a & Shuajiang Tu a b
a College of Chemistry and Chemical Engineering,
Xuzhou Normal University, Xuzhou, Jiangsu, China
b Key Laboratory of Biotechnology for Medicinal
Plant, Xuzhou, Jiangsu, China
Available online: 25 Feb 2009
To cite this article: Liangce Rong, HongXia Han, Hong Jiang, Qiya Zhang &
Shuajiang Tu (2009): Efficient One-Pot Synthesis of 4-Aryl-3-cyano-2,5-dihydro-1H-
indeno[1,2-b]pyridin-2-one and 4-Aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-
one Derivatives Under Solvent-Free Conditions, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry, 39:6,
1027-1034
To link to this article: http://dx.doi.org/10.1080/00397910802463878

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Synthetic Communications1, 39: 1027–1034, 2009
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910802463878
Efficient One-Pot Synthesis of
4-Aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]
pyridin-2-one and 4-Aryl-3-cyano-1,2,5,6-
tetrahydrobenzo[h]quinolin-2-one Derivatives
Under Solvent-Free Conditions
Liangce Rong,1,2 HongXia Han,1 Hong Jiang,2 Qiya Zhang,1
and Shuajiang Tu1,2
1College of Chemistry and Chemical Engineering, Xuzhou Normal
University, Xuzhou, Jiangsu, China
2Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou,
Jiangsu, China
Abstract: 4-Aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]pyridin-2-one and 4-aryl-
3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-one have been prepared from
indan-1-one or 3,4-dihydronaphthalen-1(2H)-one, aromatic aldehydes, 2-cyano-
acetamide, in the presence of sodium hydroxide under solvent-free conditions.
The rapid and facile method produced products in high yields.
Keywords: 2-Cyanoacetamide, 3-cyano-2-pyridones, one-pot reactions, solvent
free, synthesis
There has been a gradual change from classical reaction conditions to
more environmentally friendly routes.[1] This growth of green chemistry
holds significant potential for reduction of the by-products, waste
production and lowering of energy costs. As one of efficient synthetic
methods of green chemistry, solvent-free synthesis is now used in a lot
of chemical transformations for the synthesis of various compounds.[2]
Received May 7, 2008.
Address correspondence to Liangce Rong, College of Chemistry and
Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116,
China. E-mail: lcrong2005@yahoo.com
1027

1028
L. Rong et al.
The most evident improvements are reduced reaction times and cleaner
reactions because of fewer side products.
By virtue of the convergence of productivity, facile execution, and
generally high yield of products, one-pot multicomponent reactions
(MCRs) have attracted considerable attention from the point of
view of ideal synthesis.[3] However, if the one-pot MCRs could be carried
out under solvent-free conditions, it would be the most efficient synthetic
methods of organic synthesis. As part of our continued interest[4] in the
development of facile methods for the synthesis of organic compounds,
herein we report a very simple and highly efficient method for the syn-
thesis of 4-aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]pyridin-2-one and
4-aryl-3-cyano-1,2,5,6-tetrahydro-benzo[h]quinolin-2-one derivatives via
a
three-component cyclocondensation reaction under solvent-free
conditions.
Substituted 3-cyano-2-pyridones derivatives are important intermedi-
ates in the pharmaceutical, dye, and photo industries. Synthesis of these
compounds have been widely studied using conventional heating in the
presence of various catalysts and usually in polar solvents.[5–7] However,
in reported literature, the organic solvent was necessary. In our recent
research, we found these compounds also could be synthesized under sol-
vent-free conditions. In the typical experimental procedure, indan-1-one,
aromatic aldehydes, and 2-cyanoacetamide were mixed thoroughly with
0.2 g sodium hydroxide. The reaction mixture was heated at 70 ꢀC for
about 10–15 min and the 4-aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]
pyridin-2-one was afforded in excellent yields. To expand this reaction,
3,4-dihydronaphthalen-1(2H)-one was chosen to react with aromatic
aldehydes and 2-cyanoacetamide under similar conditions. The reactions
also could be carried out smoothly, and 4-aryl-3-cyano-1,2,5,6-tetrahy-
drobenzo[h ]quinolin-2-one could be obtained with high yields (Scheme 1).
All structures of the compounds were confirmed from IR, 1H NMR,
and elemental analyses. The x-ray diffraction analysis of crystal 4 h[8]
Scheme 1. The reaction of indan-1-one or 3,4-dihydronaphthalen-1(2H)-one,
aromatic aldehydes, and 2-cyano-acetamide.

Synthesis of Pyridin-2-one and Quinolin-2-one
1029
Table 1. The reaction results for compounds 4
Entry
R
n
Product
Yields
1
2
3
4
5
6
7
8
9
10
11
12
13
14
4-Br
4-F
2-Cl
4-Cl
2,4-Cl2
3,4-Cl2
4-CH3O
4-F
4-Br
2-Cl
1
1
1
1
1
1
1
2
2
2
2
2
2
2
4a
4b
4c
4d
4e
4f
85
90
89
90
92
88
86
95
84
85
90
89
82
88
4g
4h
4i
4j
4-Cl
4k
4l
3,4-Cl2
4-CH3
4-CH3O
4m
4n
further confirmed the structures (Fig. 1). Our observations are recorded
in Table 1.
In conclusion, we have demonstrated a novel, one-pot, three-
component reaction under solvent-free conditions that offers a facile
and efficient route for the synthesis of 4-aryl-3-cyano-2,5-dihydro-
1H-indeno[1,2-b]pyridin-2-one and 4-aryl-3-cyano-1,2,5,6-tetrahydro-
benzo[h]quinolin-2-one derivatives. This method has some advantages,
Figure 1. Structure of compound 4h.

1030
L. Rong et al.
such as shorter reaction times, milder conditions, simplicity of the
reaction, and good product yields.
EXPERIMENTAL
Melting points were uncorrected. IR spectra were recorded on a
Tensor 27 spectrometer in KBr. 1H NMR spectra were obtained in
DMSO-d6 solution with Me4Si as internal standard using a Bruker-
400 spectrometer. Elemental analyses were carried out using Perkin-
Elmer 240 II analyzer. X-ray diffraction was measured on a Siemens
P4 diffractometer.
General Procedure for the Syntheses of 4-Aryl-3-cyano-2,5-dihydro-1H-
indeno[1,2-b]pyridin-2-one and 4-Aryl-3-cyano-1,2,5,6-tetrahydro-
benzo[h]quinolin-2-one
The general procedure is represented as follows: indan-1-one (or 3,4-
dihydronaphthalen-1(2H)-one) 1 (2 mmol), aromatic aldehyde 2 (2 mmol),
2-cyanoacetamide 3 (2 mmol), and NaOH (5 mmol) were added to a flask
ꢀ
at 70 C. The reaction could be completed within 10–15 min, and the
reaction mixture was poured into water. The product was filtered, dried,
and recrystallized from 25–30 mL 95% ethanol.
Data
Compound 4a
1
Mp > 300 ꢀC; IR (KBr) v: 3241 (NH), 2222 (CN), 1636 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.66 (2H, s, CH2), 7.50–7.53
(2H, m, ArH), 7.63 (3H, t, J ¼ 7.8, 8.4 Hz, ArH), 7.70 (2H, d, J ¼ 7.8 Hz,
Hz, ArH), 8.17 (1H, d, J ¼ 2.0 Hz, ArH), 13.65 (1H, s, NH). Anal. calcd.
for C19H11BrN2O: C, 62.83; H, 3.05; N, 7.71. Found: C, 62.62; H, 3.10;
N, 7.87.
Compound 4b
1
Mp > 300 ꢀC; IR (KBr) v: 3287 (NH), 2221 (CN), 1636 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.67 (2H, s, CH2), 7.50 (2H, t,
J ¼ 3.6, 3.6 Hz, ArH), 7.63 (1H, d, J ¼ 6.0 Hz, ArH), 7.67 (4H, t,
J ¼ 8.4, 8.4 Hz, ArH), 7.17 (1H, d, J ¼ 6.0 Hz, ArH), 13.64 (1H, s, NH).
Anal. calcd. for C19H11FN2O: C, 75.49; H, 3.67; N, 9.27. Found: C,
75.60; H, 3.57; N, 9.34.

Synthesis of Pyridin-2-one and Quinolin-2-one
1031
Compound 4c
1
Mp> 300 ꢀC; IR (KBr) v: 3337 (NH), 2222 (CN), 1698 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.50 (2H, dd, J ¼ 22.4 Hz,
J ¼ 22.4 Hz, CH2), 7.54 (2H, t, J ¼ 3.6. 3.6 Hz, ArH), 7.58 (2H, br, ArH),
7.62 (2H, t, J ¼ 4.0, 4.0 Hz, ArH), 7.72 (1H, d, J ¼ 7.2 Hz, ArH), 8.20
(1H, d, J ¼ 4.0 Hz, ArH), 13.68 (1H, s, NH). Anal. calcd. for C19H11ClN2O:
C, 71.59; H, 3.48; N, 8.79. Found: C, 71.39; H, 3.56; N, 8.84.
Compound 4d
1
Mp > 300 ꢀC; IR (KBr) v: 3296 (NH), 2219 (CN), 1637 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.68 (2H, s, CH2), 7.53 (2H, t,
J ¼ 5.6. 5.6 Hz, ArH), 7.64 (1H, d, J ¼ 5.6 Hz, ArH), 7.70 (4H, dd,
J ¼ 8.4 Hz, J ¼ 8.4 Hz, ArH), 8.19 (1H, d, J ¼ 5.6 Hz, ArH), 13.68 (1H,
s, NH). Anal. calcd. for C19H11ClN2O: C, 71.59; H, 3.48; N, 8.79. Found:
C, 71.36; H, 3.58; N, 8.86.
Compound 4e
1
Mp > 300 ꢀC; IR (KBr) v: 3291 (NH), 2223 (CN), 1635 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 4.13 (2H, s, CH2), 7.50–7.54
(1H, m, ArH), 7.52 (2H, t, J ¼ 6.4, 6.4 Hz, ArH), 7.84 (2H, t, J ¼ 6.4,
6.4 Hz, ArH), 7.89 (1H, d, J ¼ 6.8 Hz, ArH), 8.00 (1H, s, ArH), 13.85
(1H, s, NH). Anal. calcd. for C19H10Cl2N2O: C, 64.61; H, 2.85; N,
7.93. Found: C, 64.91; H, 2.75; N, 7.83.
Compound 4f
1
Mp > 300 ꢀC; IR (KBr) v: 3339 (NH), 2219 (CN), 1658 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.71 (2H, s, CH2), 7.54 (2H, t,
J ¼ 6.0 Hz, J ¼ 7.2 Hz, ArH), 7.66 (1H, d, J ¼ 7.2 Hz, ArH), 7.69 (1H,
d, J ¼ 8.4 Hz, ArH), 7.89 (1H, d J ¼ 8.0 Hz, ArH), 8.04 (1H, d, J ¼ 7.6 Hz,
Hz, ArH), 8.19–8.21 (1H, br, ArH), 13.76 (1H, s, NH). Anal. calcd. for
C19H10Cl2N2O: C, 64.61; H, 2.85; N, 7.93. Found: C, 64.47; H, 2.91;
N, 7.86.
Compound 4g
1
Mp > 300 ꢀC; IR (KBr) v: 3292 (NH), 2219 (CN), 1637 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 3.72 (2H, s, CH2), 3.87 (3H,

1032
L. Rong et al.
s, OCH3), 7.14 (2H, t, J ¼ 8.8, 8.8 Hz, ArH), 7.52 (2H, t, J ¼ 3.6, 3.6 Hz,
ArH), 7.66 (1H, m, ArH), 7.89 (2H, d, J ¼ 8.8 Hz, ArH), 8.17 (1H, br,
ArH), 13.59 (1H, s, NH). Anal. calcd. for C20H14N2O2: C, 76.42; H,
4.49; N, 8.91. Found: C, 76.62; H, 4.41; N, 8.80.
Compound 4h
1
Mp > 300 ꢀC; IR (KBr) v: 3131 (NH), 2220 (CN), 1634 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.33 (2H, br, CH2), 2.74 (2H, t,
J ¼ 7.2, 7.2 Hz, CH2), 7.35 (1H, d, J ¼ 6.4 Hz, ArH), 7.39–7.46 (4H, m,
ArH), 7.52 (2H, dd, J ¼ 5.2 Hz, J ¼ 5.6 Hz, ArH), 8.07 (1H, br, ArH),
12.77 (1H, s; NH). Anal. calcd. for C20H13FN2O: C, 75.94; H, 4.14; N,
6.01. Found: C, 75.63; H, 4.07; N, 6.12.
Compound 4i
1
Mp > 300 ꢀC; IR (KBr) v: 3124 (NH), 2221 (CN), 1638 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.36 (2H, t, J ¼ 6.0, 6.0 Hz, CH2),
2.76 (2H, t, J ¼ 6.8, 6.8 Hz, CH2), 7.35 (1H, d, J ¼ 6.8 Hz, ArH), 7.43
(4H, dd, J ¼ 8.4 Hz, J ¼ 8.4 Hz, ArH), 7.78 (2H, d, J ¼ 8.8 Hz, ArH), 8.07
(1H, d, J ¼ 7.6 Hz, ArH), 12.62 (1H, s, NH). Anal. calcd. for C20H13BrN2O:
C, 63.68; H, 3.47; N, 7.43. Found: C, 63.40; H, 3.51; N, 7.54.
Compound 4j
1
Mp > 300 ꢀC; IR (KBr) v: 3132 (NH), 2221 (CN), 1638 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.37 (2H, br, CH2), 2.76 (2H, t,
J ¼ 6.8, 6.8 Hz, CH2), 7.35 (1H, d, J ¼ 7.2 Hz, ArH), 7.44 (4H, dd,
J ¼ 8.0 Hz, J ¼ 8.0 Hz, ArH), 7.78 (2H, d, J ¼ 8.4 Hz, ArH), 8.07 (1H,
d, J ¼ 7.6 Hz, ArH), 12.66 (1H, s, NH). Anal. calcd. for C20H13ClN2O:
C, 72.18; H, 3.94; N, 8.42. Found: C, 72.40; H, 3.92; N, 8.52.
Compound 4k
1
Mp > 300 ꢀC; IR (KBr) v: 3130 (NH), 2223 (CN), 1637 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.37 (2H, br, CH2), 2.76 (2H, t,
J ¼ 6.8, 6.8 Hz, CH2), 7.35 (1H, d, J ¼ 7.2 Hz, ArH), 7.43 (2H, dd,
J ¼ 7.2 Hz, J ¼ 7.2 Hz, ArH), 7.49 (2H, d, J ¼ 8.0 Hz, ArH), 7.64 (2H,
d, J ¼ 8.4 Hz, ArH), 8.07 (1H, d, J ¼ 7.6 Hz, ArH), 12.62 (1H, s, NH).
Anal. calcd. for C20H13ClN2O: C, 72.18; H, 3.94; N, 8.42. Found: C,
72.40; H, 3.85; N, 8.55.

Synthesis of Pyridin-2-one and Quinolin-2-one
1033
Compound 4l
Mp 287–289 ꢀC; IR (KBr) v: 3123 (NH), 2218 (CN), 1635 (CO) cmꢁ1; 1H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.28 (1H, t, J ¼ 7.2, 6.8 Hz, CH2),
2.38 (1H, t, J ¼ 6.8, 7.2 Hz, CH2),2.75 (2H, t, J ¼ 6.8 Hz, J ¼ 8.0 Hz,
CH2), 7.23–7.30 (1H, m, ArH), 7.35–7.48 (3H, m, ArH), 7.69–7.85 (2H,
m, ArH), 8.03–8.09 (1H, m, ArH), 12.54 (1H, s, NH). Anal. calcd. for
C20H12Cl2N2O: C, 65.41; H, 3.29; N, 7.63. Found: C, 65.66; H, 3.22;
N, 7.51.
Compound 4m
1
Mp > 300 ꢀC; IR (KBr) v: 3128 (NH), 2221 (CN), 1634 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.37 (2H, br, CH2), 2.40 (3H, s,
CH3), 2.76 (2H, t, J ¼ 7.2, 7.2 Hz, CH2), 7.31 (2H, d, J ¼ 8.4 Hz, ArH),
7.36 (3H, d, J ¼ 8.4 Hz, ArH), 7.43 (2H, t, J ¼ 6.4 Hz, J ¼ 7.2 Hz, ArH),
8.07 (1H, d, J ¼ 8.4 Hz, ArH), 12.65 (1H, s, NH). Anal. calcd. for
C21H16N2O: C, 80.75; H, 5.16; N, 8.97. Found: C, 80.36; H, 5.21; N, 8.87.
Compound 4n
1
Mp > 300 ꢀC; IR (KBr) v: 3120 (NH), 2219 (CN), 1636 (CO) cmꢁ1; H
NMR (400 MHz, DMSO-d6) (d, ppm): 2.41 (2H, t, J ¼ 6.0, 7.2 Hz,
CH2), 2.75 (2H, t, J ¼ 6.0, 7.2 Hz, CH2), 3.84 (3H, s, CH3O), 7.11 (2H,
d, J ¼ 8.8 Hz, ArH), 7.34 (1H, d, J ¼ 6.8 Hz, ArH), 7.38 (3H, d,
J ¼ 8.8 Hz, ArH), 7.43 (1H, t, J ¼ 7.2, 7.2 Hz, ArH), 8.06 (1H, d,
J ¼ 7.2 Hz, ArH), 12.58 (1H, s, NH). Anal. calcd. for C21H16N2O2: C,
76.81; H, 4.91; N, 8.53. Found: C, 76.55; H, 4.86; N, 8.62.
ACKNOWLEDGMENTS
We thank the Natural Science Foundation of Jiangsu Education Depart-
ment (No. 08KJB150017), the National Natural Science Foundation of
China (No. 20772103), and the PeiYu Foundation (No. 07PYL06) of
Xuzhou Normal University for financial support.
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ˆ
of 2(1H)-pyridinones from a-aminoenones and malononitrile: Reaction
mechanism. J. Org. Chem. 1999, 64, 9493–9498.
8. X-ray crystallography for 4h: empirical formula C20H13FN2O, Fw ¼ 316.32,
˚
˚
ꢀ
˚
T ¼ 298(2) K, triclinic, space group p–1, a ¼ 8.116 (10) A, b ¼ 9.278 (12) A,
ꢀ
ꢀ
˚
c ¼ 11.263 (14) A, a ¼ 98.674 (19) , b ¼ 105.095 (17) , c ¼ 104.846 (18) ,
3
˚
V ¼ 769.7 (16) A , Z ¼ 2, Dcalcd. ¼ 1.365 Mg=m3, k (MoK) ¼ 0.71073 A,
m ¼ 0.094 mmꢁ1, F(000) ¼ 328. 2.34ꢀ < h < 25.001ꢀ, R ¼ 0.0482, wR ¼ 0.1149,
ꢁ3
˚
s ¼ 0.997, largest diff. peak and hole: 0.149 and ꢁ0.168 e A
.