JOURNAL OF CHEMICAL RESEARCH 2016 491
References
the capillary tube method with an Electrothermal 9100 apparatus.
Elemental analyses were performed using a Heraeus CHN–O–Rapid
analyser. IR spectra were recorded on a Shimadzu spectrometer 883
1
2
3
4
D. Seebach and J.L. Matthews, Chem. Commun., 1997, 2015.
A.Y. Shen, C.T. Tsai and C.L. Chen, Eur. J. Chem., 1997, 34, 877.
X.H. Cai. H. Guo and B. Xie, Int. J. Chem., 2011, 3, 119.
M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare and V. Khaky-
Zadeh, Applied Catal. A: General, 2011, 400, 70.
1
(KBr pellets, Nujol mulls, 4000–400 cm−1). H NMR spectra were
recorded on a Bruker-Avance DRX 400 spectrometer using TMS as an
external standard.
5
6
A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, F. Abi, A. Zare, H.
Kaveh, V. Khakyzadeh, K. Rostami, A. Parhami and H. Torabi-Monfared,
Tetrahedron, 2013, 9, 212.
A. Zare, S. Akbarzadeh, E. Foroozani, H. Kaveh, A.R. Moosavi-Zare, A.
Hasaninejad, M. Mokhlesi, M.H. Beyzavi and M.A. Zolfigol, J. Sulfur
Chem., 2012, 23, 259.
A. Zare, A. Hasaninejad, E. Rostami, A.R. Moosavi-Zare, N. Pishahang,
M. Roshankar and M. Khedri, E-J. Chem., 2010, 7, 1162.
A.R. Hajipour, Y. Ghayeb, N. Sheikhan and A.E. Ruoho, Tetrahedron Lett.,
2009, 50, 5649.
Preparation of 1-amidoalkyl-2-naphtols catalysed by antimony(III)
acetate
A mixture of 2-naphthol (1 mmol, 0.144 g), 4-nitrobenzaldehyde
(1 mmol, 0.151 g), acetamide (1 mmol, 0.059 g) and antimony(III)
acetate (0.02 g) was ground in a mortar for 1 min under solvent-free
conditions at room temperature. The progress of the reaction was
monitored by TLC. After completion of the reaction, the crude solid
product was dissolved in CH2Cl2. The mixture was filtered to separate
the catalyst. The catalyst was washed with CH2Cl2 (2 × 5 mL). The
recovered catalyst was dried in vacuo and used in subsequent catalytic
runs. The product was washed with cold diethyl ether (10 mL) and
recrystallisation from MeOH afforded pure products.
7
8
9
A.R. Supale and G.S. Gokavi, J. Chem. Sci., 2010, 122, 189.
10 B. Adrom, N. Hazeri, M.T. Maghsoodlou and M. Mollamohammadi, Res.
Chem. Intermed., 2015, 41, 4741.
N-[(2-hydroxy-3-methoxyphenyl)(2-hydroxynaphthalen-1-yl)
11 N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Aboonajmi and
M. Safarzaei, Chem. Sci. Trans., 2013, 2(S1), S330.
12 M. Kamali, Der Pharma Chem., 2015, 7, 318.
13 M. Hajjami, A. Ghorbani-Choghamarani and F. Gholamian, Bulgar. Chem.
Commun., 2015, 47, 119.
14 N.P. Selvam and P.T. Perumal, Tetrahedron Lett., 2006, 47, 7481.
15 B. Das, K. Laxminarayana, B. Ravikanth and B.R. Rao, J. Mol. Catal. A:
Chem., 2007, 261, 180.
methyl]acetamide (3j): Yellow powder; m.p. 157–159 °C; IR (νmax
/
cm–1) KBr: 3347, 3321, 1635; Anal. calcd for C20H19NO4: C, 71.20; H,
5.68; N, 4.15; found: C, 71.38; H, 5.54; N, 4.29%; MS (m/z, %): 337
1
(6); H NMR (400 MHz, DMSO-d6): δ 2.02 (3H, s, CH3), 3.73 (3H,
3
s, OCH3), 5.11 (1H, broad s, OH), 6.16 (1H, d, JHH = 8 Hz, NCH),
7.04–7.74 (9H, m, ArH), 8.00 (1H, d,3JHH = 8 Hz, NH), 9.53 (1H, broad
s, OH). 13C NMR (100.6 MHz, DMSO-d6): δ 21.4 (CH3), 37.2 (CH),
55.2 (OCH3), 112.1, 115.3, 118.7, 119.6, 121.0, 122.0, 123.9, 126.3,
128.3, 129.2, 129.4, 130.1, 133.0, 143.0, 151.8, 152.1, 173.0.
16 S. Kantevari, S.V.N. Vuppalapati and L. Nagarapu, Catal. Commun., 2007,
8, 1857.
17 L. Nagarapu, M. Baseeruddin, S. Apuri and S. Kantevari, Catal. Commun.,
2007, 8, 1729.
18 H.R. Shaterian and H. Yarahmadi, Tetrahedron Lett., 2008, 49, 1297.
19 H.R. Shaterian, H. Yarahmadi and M. Ghashang, Tetrahedron, 2008, 64,
1263.
Methyl 4-[acetylamino(2-hydroxynaphtalen-1-yl)methyl]benzoate
(3k): Pale brown powder; m.p. 220–222 °C; IR (νmax cm–1) KBr: 3343,
/
3310, 1743, 1641; Anal. calcd for C21H19NO4: C, 72.19; H, 5.48; N, 4.01;
1
found: C, 72.01; H, 5.34; N, 4.23%; MS (m/z, %): 349 (3); H NMR
(400 MHz, DMSO-d6): δ 2.10 (3H, s, CH3), 3.79 (3H, s, OCH3),
3
20 H.R. Shaterian and H. Yarahmadi, Arkivoc, 2008, (ii), 105.
21 H.R. Shaterian, A. Amirzadeh, F. Khorami and M. Ghashang, Synth.
Commun., 2008, 38, 2983.
22 M.M. Khodaei, A.R. Khosropour and H. Moghanian, Synlett, 2006, 916.
23 S.B. Patil, P.R. Singh, M.P. Surpur and S.D. Samant, Ultrason. Sonochem.,
2007, 14, 515.
6.24 (1H, d, JHH = 8 Hz, NCH), 6.73–7.86 (10H, m, ArH), 8.13 (1 H,
d, 3JHH = 8 Hz, NH), 9.55 (1 H, broad s, OH); 13C NMR (100.6 MHz,
DMSO-d6): δ 23.3 (CH3), 48.6 (CH), 51.4 (OCH3), 115.4, 117.5, 118.8,
119.3, 122.1, 122.5, 123.2, 126.3, 128.1, 128.8, 130.4, 133.3, 147.2,
153.4, 167.9, 171.3.
N-[(2-hydroxynaphthalen-1-yl)(4-methylaminophenyl)methyl]
24 G. Srihari, M. Nagaraju and M.M. Murthy, Helv. Chim. Acta, 2007, 90,
1497.
acetate (3l): Brown powder; m.p. 121–123 °C; IR (KBr) (νmax
/
cm–1): 3350, 3345, 1681; Anal. calcd for C20H20N2O2: C, 74.98; H,
25 H. Taghrir, M. Ghashang and M. Najafi Biregan, Chin. Chem. Lett., 2016,
27, 119.
26 A.R. Kiasat, L. Hemat-Alian and S.J. Saghanezhad, Res. Chem. Intermed.,
2016, 915.
6.29; N, 8.74; found: C, 75.13; H, 6.41; N, 8.90%; MS (m/z, %): 320
1
(5); H NMR (400 MHz, DMSO-d6): δ 2.17 (3H, s, CH3), 2.69 (3H,
3
s, NCH3), 3.90 (1H, broad s, NH), 6.23 (1H, d, JHH = 8 Hz, NCH),
6.85–7.64 (10H, m, ArH), 8.16 (1 H, d, 3JHH = 8 Hz, NH), 9.67 (1 H,
broad s, OH); 13C NMR (100.6 MHz, DMSO-d6): δ 23.5 (CH3), 29.6
(NCH3), 48.5 (CH), 114.2, 115.3, 118.8, 121.9, 123.3, 126.8, 128.7,
128.9, 129.6, 133.5, 145.2, 131.3, 134.0, 153.2, 172.1.
27 Z. Karimi-Jaberi, M. Jokar and S.Z. Abbasi, J. Chem., 2013, Article ID:
341649.
28 Q. Zhang, J. Luo and Y. Wei, Green Chem., 2010, 12, 2247.
29 J. Luo and Q. Zhang, Monatsh. Chem., 2011, 142, 923.
30 B.F. Mirjalili, A. Bamoniri and L. Rahmati, Arab. J. Chem., 2016,
The Research Council of Payamenoor University is gratefully
acknowledged for the financial support for this work.
31 S. Habibzadeh and H. Ghasemnejad, J. Chin. Soc., 2012, 59, 193.
32 B. Datta and M.A. Pasha, Ultrason. Sonochem., 2010, 18, 624.
33 M.M. Heravi, N. Tavakoli-Hoseini and F.F. Bamoharram, Synth. Commun.,
2011, 41, 298.
Received 7 April 2016; accepted 3 June 2016
Published online: 22 July 2016