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RSC Advances
Page 7 of 9
DOI: 10.1039/C5RA20718E
Journal Name
ARTICLE
1
was responsible for its excellent catalytic activity. The present 1259, 1137, 1025, 938, 807, 732; H NMR (400 MHz, C6D6) δ = 7.93
method offers advantages over the reported methods such as easy (d, J = 7.6 Hz, 1H), 7.55 (d, J = 8.4 Hz, 1H), 7.19-7.16 (m, 2H), 7.16-
recoverability of catalyst by external magnetic field, recyclability for 7.13 (m, 2H), 7.10 (t, J = 7.6 Hz, 1H), 7.04-7.01 (m, 2H), 6.76 (s, 1H),
six times, green reaction conditions, wide substrate scope, high 6.38 (t, J = 6.8 Hz, 1H), 6.10 (t, J = 6.8 Hz, 1H), 3.11 (t, J = 4.6 Hz, 4H),
catalytic activity, short reaction time etc. The further study on 3.08 (t, J = 4.6 Hz, 4H), 2.34 (s, 3H) ppm; 13C NMR (100 MHz, C6D6) δ
catalytic potential of Cu@Fe2O3 is underway in our laboratory.
= 150.92, 131.99, 131.48, 130.02, 128.92, 125.62, 124.55, 122.19,
120.97, 119.01, 118.14, 116.83, 113.12, 109.69, 105.14, 53.31,
51.34, 16.70 ppm; HRMS (ES): Calcd 373.1613, found 373.1609;
Anal. calcd for C23H23N3S: C, 73.96; H, 6.21; N, 11.25; S, 8.58: found
C, 73.78; H, 6.42; N, 11.04; S, 8.38:
Experimental Section
Typical procedure for the synthesis of Cu@Fe2O3 MNPs: The
synthesis of Cu@Fe2O3 MNPs was achieved by hydrothermal
method. Typically, 10 mL of 0.2 M FeCl3 aqueous solution (2 mmol,
0.324 g) and 10 mL of 2.0 M aqueous urea solution (20 mmol, 1.2 g)
were mixed in 10 mL of ethylene glycol. To this mixture, 10 mL of
0.2 M CuCl2 aqueous solution (2 mmol, 0.27 g) and glucose (10
mol%) and 5 mL of 20.6 M (40 %) aqueous NH3 were mixed
successively and sonicated for 15 min to form a homogeneous
mixture. The resulted mixture was transferred into a 100 ml Teflon-
lined stainless-steel autoclave and heated at 180 oC for 8h. The
autoclave was allowed to cool naturally to room temperature. The
resulting solid nanoparticles were washed several times with water
followed by final wash with acetone and recovered by using external
magnetic field. The obtained MNPs were collected and dried in oven
at 70 oC for 6 h.
N-Methyl-N,1-diphenylpyrrolo[1,2-a]quinolin-3-amine
(4bba):
Yellow oil. IR (υmax/cm-1, CHCl3): 2926, 2809, 2359, 1598, 1496,
1449, 1320.39, 1114, 796, 751; 1H NMR (400 MHz, C6D6) δ = 7.63 (d,
J = 8.3 Hz, 1H), 7.32 (d, J = 7.6 Hz, 2H), 7.27 (d, J = 7.6 Hz, 1H), 7.23
(t, J = 7.6 Hz, 2H), 7.12-709 (m, 3H), 6.90 (d, J = 7.6 Hz, 2H), 6.82 (t, J
= 6.8 Hz, 1H), 6.77 (d, J = 8.3 Hz, 1H), 6.63 (d, J = 9.1 Hz, 1H), 6.52 (s,
1H), 3.12 (s, 3H) ppm; 13C NMR (100 MHz, C6D6) δ = 150.54, 135.86,
134.62, 129.52, 129.28, 128.73, 126.69, 126.15, 123.63, 119.05,
117.98, 117.63, 117.33, 114.60, 113.85 ppm; HRMS (ES): Calcd
348.1626, found 348.1624; Anal. calcd for C25H20N2: C, 86.17; H,
5.79; N, 8.04; found C, 86.15; H, 5.81; N, 8.16.
3-(3-Methylpiperidin-1-yl)-1-phenylpyrrolo [1,2-a]quinoline (4bca):
Yellow oil. IR (υmax/cm-1, CHCl3): 3059, 2926, 2850, 1607, 1492,
1451, 1374, 1317, 1190, 1126, 791, 755, 700; 1H NMR (400 MHz,
C6D6) δ = 7.59 (t, J = 9.1 Hz, 2H), 7.36 (d, J = 7.6 Hz, 2H), 7.33 (d, J =
7.6 Hz, 1H), 7.12-7.09 (m, 2H), 6.93 (t, J = 7.6 Hz, 1H), 6.78 (t, J = 6.8
Hz, 1H), 6.71 (d, J = 9.2 Hz, 1H), 6.58 (s, 1H), 3.24 (t, J = 10.7 Hz, 2H),
2.64 (t, J = 11.4 Hz, 1H), 2.36 (t, J = 10.6 Hz, 1H), 1.83-1.76 (m, 1H),
1.69-1.58 (m, 2H), 0.96-0.89 (m, 1H), 0.85 (d, J = 6.8 Hz, 3H) ppm.
13C NMR (100 MHz, C6D6) δ = 136.43, 134.80, 134.09, 129.44,
128.69, 128.59, 127.50, 126.68, 126.27, 124.83, 123.39, 118.06,
116.79, 109.49, 62.93, 55.25, 33.20, 31.88, 26.39, 19.68 ppm. HRMS
(ES): Calcd 340.1939, found 340.1940; Anal. calcd for C24H24N2: C,
84.67; H, 7.11; N, 8.23; found C, 84.57; H, 7.16; N, 8.28.
General Procedure for synthesis of aminoindolizines and
pyrrolo[1,2-a]quinolines (4):
carboxaldehye/quinolin-2-carboxaldehyde
mmol), phenylacetylenes (1 mmol) and Cu@Fe2O3 catalyst (5 mg)
A
mixture of pyridine-2-
1
(1 mmol), amines (1
2
3
o
were stirred at 110 C in glycerin (2 mL). The progress of reaction
was monitored by TLC until the reaction was completed. After
completion of reaction, the glycerin was removed by addition of
water followed by decanting the reaction mixture. Ethanol was
added to this mixture followed by recovery of Cu@Fe2O3 catalyst by
external magnet. The recovered catalyst was washed with ethanol for
3-4 times and dried at 80 oC in oven to reuse it for further. The
combined organic layers were evaporated and the obtained crude
products were purified by flash column chromatography.
4-(1-Phenylpyrrolo[1,2-a]quinolin-3-yl)thiomorpholine
(4bda):
Yellow oil. IR (υmax/cm-1, CHCl3): 2923, 2854, 2358, 1600, 1459,
1
1374, 1075, 966, 760; H NMR (400 MHz, C6D6) δ = 7.57 (d, J = 8.3
Hz, 1H), 7.38 (d, J = 9.1 Hz, 1H), 7.34-7.31 (m, 3H), 7.12-7.10 (m,
3H), 6.92 (t, J = 7.6 Hz, 1H), 6.77 (t, J = 8.3 Hz, 1H), 6.71 (d, J = 9.9
Hz, 1H), 6.47 (s, 1H), 3.11 (t, J = 5.3 Hz, 4H), 2.58 (t, J = 4.5 Hz, 4H)
ppm; 13C NMR (100 MHz, C6D6) δ = 136.00, 134.41, 133.53, 129.26,
128.51, 128.45, 126.25, 124.82, 123.33, 117.84, 117.31, 117.13,
109.58, 56.30, 28.44 ppm; HRMS (ES): Calcd 344.1347, found
344.1341; Anal. calcd for C22H20N2S: C, 76.71; H, 5.85; N, 8.13; S,
9.31; found C, 76.68; H, 5.79; N, 8.19; S, 9.30.
Experimental data for unknown compounds
1-(3-Methylpiperidin-1-yl)-3-(pyridin-2-yl)indolizine (4acg): Yellow
oil. IR (υmax/cm-1, CHCl3): 2936, 2842, 1734, 1628, 1531, 1448, 1309,
956, 745; 1H NMR (400 MHz, C6D6) δ = 10.37 (d, J = 6.9 Hz, 1H), 8.45
(d, J = 6.1 Hz, 1H), 7.55 (d, J = 9.2 Hz, 1H), 7.27 (d, J = 8.4 Hz, 1H),
7.10 (t, J = 7.6 Hz, 1H), 7.06 (s, 1H), 6.52 (t, J = 6.1 Hz, 1H), 6.47 (t, J
= 7.6 Hz, 1H), 6.35 (t, J = 6.9 Hz, 1H), 3.22 (d, J = 7.6 Hz, 2H), 2.59 (t,
J = 11.4 Hz, 1H), 2.34 (t, J = 10.7 Hz, 1H), 1.92-1.64 (m, 5H), 0.88 (d, J
= 6.7 Hz, 3H) ppm; 13C NMR (100 MHz, C6D6) δ = 153.31, 148.44,
135.73, 132.22, 127.29, 119.86, 118.66, 117.45, 116.92, 111.81,
107.17, 62.68, 54.98, 33.31, 31.96, 26.41, 19.74 ppm; HRMS (ES):
Calcd 291.1735, found 291.1721; Anal. calcd for C19H21N3: C,
78.32; H, 7.26; N, 14.42; found C, 78.22; H, 7.41; N, 14.24.
1-(4-Fluorophenyl)-3-(3-methylpiperidin-1-yl)pyrrolo[1,2-a]quinoline
(4bfd): Yellow oil. IR (υmax/cm-1, CHCl3): 2945, 2817, 2359, 1601,
1
1493, 1371, , 1225, 1146, 969, 794, 757; H NMR (400 MHz, C6D6) δ
= 7.48 (d, J = 9.1 Hz, 1H), 7.38 (d, J = 8.3 Hz, 1H), 7.30 (d, J = 8.3 Hz,
1H), 7.14 (d, J = 7.6 Hz, 2H), 7.04-7.01 (m, 3H), 6.96 (t, J = 7.6 Hz,
1H), 6.90 (t, J = 7.6 Hz, 1H), 6.78 (d, J = 7.6 Hz, 1H), 6.73 (t, J = 8.3
Hz, 2H), 6.68 (d, J = 9.1 Hz, 1H), 6.43 (s, 1H), 3.06 (t, J = 4.5 Hz, 4H),
2.92 (t, J = 4.5 Hz, 4H), 2.29 (s, 3H) ppm; 13C NMR (100 MHz, C6D6) δ
3-(Thiophen-3-yl)-1-(4-o-tolylpiperazin-1-yl)indolizine (4afe): Yellow
oil; IR (υmax/cm-1, CHCl3): 2930, 2816, 1599, 1549, 1498, 1434, 1366,
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