Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide

Ahmad Poursattar Marjani 1 , Jabbar Khalafy 1 , and Somayeh Akbarzadeh 1
  • 1 Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran
Ahmad Poursattar Marjani
  • Corresponding author
  • Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran
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, Jabbar Khalafy
  • Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran
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and Somayeh Akbarzadeh
  • Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran
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Abstract

Pyrazolopyridine and pyrazoloquinoline derivatives were obtained by a one-pot, three-component reaction of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide at 80°C in water through Knoevenagel and Micheal reactions, followed by intramolecular condensation, unexpected dearoylation and oxidation. Mild reaction conditions, high yields, simplicity of work up procedure, starting materials availability and clean product formation are some of the main advantages of this synthetic strategy.

1 Introduction

It has been reported that, more than 90% of compounds analysed by pharmaceutical companies are nitrogen-containing heterocycles [1], and the nitrogen-containing heterocycles exhibit excellent biological and pharmaceutical activities.

The synthesis of -pyrazolo[3,4-b]pyridine derivatives by microwave-assisted one-pot reaction between 5-aminopyrazole derivatives, paraformaldehyde and β-diketones catalyzed by InCl3 in aqueous media was recently reported [2].

The presence of pyrazoloquinoline moieties in numerous natural products makes them an important class of heterocyclic compounds with several biological and pharmacological activities, such as anti-mycobacterial [3], anti-microbial [4], antiviral [5]. Pyrazolopyridines have also received more attention because of their wide range of biological and pharmacological properties, such as anti-pyretic [6] and anxiolytic [7], antimalarial [8], and this has made such derivatives increasingly important.

The reaction of several starting materials in one pot may allow the formation of the corresponding product in high yields and minimize the use of hazardous organic solvents during separation and work-up steps which leads to a green procedure [9].

Tetrapropylammonium bromide (TPAB) is a readily available and an inexpensive catalyst with many catalytical applications in organic reactions [10,11].

Several studies have been conducted on the synthesis of a new series of heterocyclic compounds using one-pot, multicomponent reactions in our laboratory [12, 13, 14, 15, 16, 17, 18, 19, 20]. In continuation of our previous studies, we were interested to investigate the possibility of the synthesis of a new series of pyrazolopyridine and pyrazoloquinoline derivatives by the one-pot, three-component reaction of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of TPAB as a catalytic. However, surprisingly, it was found that unexpected dearoylation occurred during the reaction to provide the corresponding pyrazolopyridines and pyrazoloquinolines as the final products in high yields.

2 Experimental

All chemicals were purchased from Merck and Acros companies and used without any purification. The completion of reactions were controlled by thin layer chromatography (TLC) silica gel on aluminium plates. Melting points were measured with a Philip Harris C4954718 apparatus and are uncorrected. Infrared spectra were recorded with thermo Nicolet Nexus 670 FT-IR using KBr pellets. The 1H and 13C NMR spectra were recorded on Bruker Avance AQS 300 MHz spectrometer using CDCl3 as solvent, relative to tetramethylsilane (TMS) as the internal standard. Mass spectra were measured on a Varian Matt 311 spectrometer and high resolution spectra were obtained by Kratos MS 25RF spectrometer.

General procedure for the synthesis of products 5a-i

A mixture of arylglyoxals 1a-i (1 mmol), 3-methyl-1-aryl-1H-pyrazol-5-amines 2a-c (1 mmol) and cyclic 1,3-dicarbonyl compounds 3a-e (1 mmol) in the presence of TPAB (20 mol%) in water/acetone (1:2, 10 mL) was stirred at 80°C for an appropriate time (monitored by TLC, CH2Cl2: hexane: MeOH/15:15:1). Half of the solvent was evaporated and the precipitate was filtered and washed with H2O/EtOH (1:2) to give the desired products 5a-i in 90-98% yield.

Recovering of TPAB

After filtration of products 5a-i and washing the precipitate with water, the filtrate was extracted with CHCl3 and the aqueous phase was separated. Evaporation of water gave TPAB, which may be recrystallized from Et2O as white crystals.

3-Methyl-1-phenyl-6,7-dihydrocyclopenta[b] pyrazolo[4,3-e]pyridin-5(1H)-one (5a)

White powder; yield 96% (253 mg); mp: 213-216°C (lit. [2], 215-217°C); IR (KBr, cm-1): 2945, 2877, 1681, 1593, 1502, 1480, 1416, 1381, 1326, 1264, 1222, 1182, 1015, 912, 880, 837, 758, 688, 609; 1H NMR (CDCl3) δ (ppm) 8.36 (s, 1H, Ar), 7.79 (d, J = 8.4 Hz, 2H, Ar), 7.58 (t, J = 8.1 Hz, 2H, Ar), 7.40 (t, J = 7.5 Hz, 1H, Ar), 3.46-3.44 (m, 2H, CH2), 2.88-2.83 (m, 2H, CH2), 2.32 (s, 3H, CH3); 13C-NMR (CDCl3) δ (ppm): 192.7, 174.2, 153.7, 144.5, 140.5, 134.3, 131.6, 129.4, 122.6, 121.1, 113.7, 36.1, 29.3, 13.9; MS (EI): m/z (%): 263 [M]+ (35), 234 (10), 141 (37), 140 (12), 139 (100), 111 (46), 77 (21).

3-Methyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b] quinolin-5-one (5b)

White needles; yield 90% (249 mg); mp: 126-128°C (lit. [2], 128-130°C, and lit. [21], 123-124); IR (KBr, cm-1): 3030, 2955, 1662, 1617, 1527, 1459, 1363, 1189, 1119, 1066, 1004, 847, 754, 694; 1H-NMR (CDCl3) δ (ppm): 8.77 (s, 1H, Ar), 8.30 (d, J = 7.8 Hz, 2H, Ar), 7.53 (t, J = 7.8 Hz, 2H, Ar), 7.32 (t, J = 7.2 Hz, 1H, Ar), 3.29 (t, J = 6.3 Hz, 2H, CH2), 2.78 (t, J = 6.3 Hz, 2H, CH2), 2.68 (s, 3H, CH3), 2.25 (quin, J = 6.3 Hz, 2H, CH2); 13C-NMR (CDCl3) δ (ppm): 197.5, 163.9, 145.1, 130.5, 129.1, 126.0, 123.1, 120.9, 116.8, 116.4, 104.8, 38.9, 33.8, 22.0, 12.5; MS (EI): m/z (%): 277 [M]+ (13), 271 (11), 239 (15), 205 (13), 165 (15), 135 (92), 77 (46), 43 (100).

3,8,8-Trimethyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one (5c)

White powder; yield 92% (281 mg); mp: 167-169°C; IR (KBr, cm-1): 3347, 3067, 2959, 2936, 2869, 1683, 1593, 1504, 1481, 1417, 1380, 1269, 1235, 1121, 1090, 1012, 979, 821, 779, 750, 685, 624; 1H NMR (CDCl3) δ (ppm) 8.74 (s, 1H, Ar), 8.27 (d, J = 8.1 Hz, 2H, Ar), 7.53 (t, J = 7.2 Hz, 2H, Ar), 7.34 (t, J = 7.2 Hz, 1H, Ar), 2.55 (s, 3H, CH3), 2.27 (bs, 2H, CH2), 1.58 (bs, 2H, CH2), 1.16 (s, 6H, 2×CH3); 13C-NMR (CDCl3) δ (ppm): 196.8, 163.4, 162.3, 151.4, 144.6, 144.2, 130.8, 130.2, 128.1, 122.0, 120.3, 52.2, 47.7, 32.9, 27.0, 18.8; MS (EI): m/z (%): 305 [M]+ (5), 300 (6), 140 (32), 112 (28), 97 (14), 83 (100), 70 (19), 56 (44) and HRMS (ESI): calcd. for C19H19N3O [M]+ 305.1528; found: 305.1542.

3,7,7-Trimethyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one (5d)

White needles; yield 97% (296 mg); mp: 163-165°C (lit. [2], 165-167°C, and lit. [22], 165-166°C); IR (KBr, cm-1): 2951, 2932, 2359, 1678, 1569, 1593, 1494, 1416, 1376, 1281, 1243, 1116, 1023, 758, 679, 556; 1H NMR (CDCl3) δ (ppm) 8.74 (s, 1H, Ar), 8.30 (d, J = 9 Hz, 2H, Ar), 7.54 (d, J = 9 Hz, 2H, Ar), 7.32 (t, J = 9 Hz, 1H, Ar), 3.18 (s, 2H, CH2), 2.67 (s, 3H, CH3), 2.63 (s, 2H, CH2), 1.15 (s, 6H, 2×CH3); 13C-NMR (CDCl3) δ (ppm): 197.5, 162.6, 151.6, 145.1, 139.2, 129.9, 129.0, 125.9, 122.1, 120.9, 116.7, 52.4, 47.5, 32.9, 28.3, 12.5; MS (EI): m/z (%): 306 [M+1]+ (27), 305 [M]+ (100), 290 (8), 277 (7), 249 (43), 220 (8), 180 (15), 129 (6), 77 (14).

1-(3-Chlorophenyl)-3,7,7-trimethyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one (5e)

White solid; yield 98% (332 mg); mp: 148-150°C; IR (KBr, cm-1): 3102, 2955, 2872, 1683, 1590, 1479, 1454, 1379, 1275, 1239, 1141, 1093, 899, 872, 778, 741, 679, 554; 1H NMR (CDCl3) δ (ppm) 8.75 (s, 1H, Ar), 8.46 (s, 1H, Ar), 8.32 (d, J = 7.5 Hz, 1H, Ar), 7.45 (t, J = 7.5 Hz, 1H, Ar), 7.26 (bd, overlapped by CDCl3 impurity peak, 1H, Ar), 3.21 (s, 2H, CH2), 2.67 (s, 3H, CH3), 2.64 (s, 2H, CH2), 1.17 (s, 6H, 2×CH3); 13C-NMR (CDCl3) δ (ppm): 197.4, 162.9, 151.8, 145.6, 134.8, 131.1, 128.9, 126.7, 124.8, 124.7, 121.6, 116.9, 114.0, 52.4, 47.5, 33.0, 27.9, 13.3; MS (EI): m/z (%): 341 [M+2]+ (39), 339 [M]+ (100), 283 (45), 250 (15), 214 (13), 179 (13), 149 (13), 111 (23), 83 (47), 71 (45), 57 (42) and HRMS (ESI): calcd. for C19H18ClN3O [M]+ 339.1138; found: 339.1110.

1-(4-Chlorophenyl)-3,7,7-trimethyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one (5f)

White solid; yield 95% (322 mg); mp: 144-146°C (lit. [22], 148-149°C); IR (KBr, cm-1): 3106, 2957, 2932, 2870, 1679, 1594, 1576, 1499, 1475, 1447, 1382, 1270, 1241, 1218, 1141, 1090, 1013, 829, 691, 557, 503; 1H NMR (CDCl3) δ (ppm) 8.75 (s, 1H, Ar), 8.33 (d, J = 8.7 Hz, 2H, Ar), 7.48 (d, J = 8.7 Hz, 2H, Ar), 3.19 (s, 2H, CH2), 2.67 (s, 3H, CH3), 2.64 (s, 2H, CH2), 1.27 (s, 6H, 2×CH3); 13C-NMR (CDCl3) δ (ppm): 197.4, 163.6, 162.9, 151.8, 134.8, 131.1, 128.9, 126.7, 122.4, 121.6, 116.9, 52.3, 47.4, 33.0, 27.2, 13.3; MS (EI): m/z (%): 341 [M+2]+ (34), 339 [M]+ (98), 283 (38), 278 (100), 217 (19), 179 (14), 139 (31), 112 (30), 105 (88), 77 (41), 57 (24).

3-Methyl-1-phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one (5g)

Yellow solid; yield 91% (283 mg); mp: 245-247°C (lit. [2], 246-248°C); IR (KBr, cm-1): 3088, 2959, 2867, 1690, 1580, 1556, 1471, 1314, 1232, 1165, 1058, 947, 846, 760, 678, 593; 1H-NMR (CDCl3) δ (ppm): 8.42 (s, 1H, Ar), 8.29 (d, J = 7.2 Hz, 1H, Ar), 8.01 (d, J = 8.1 Hz, 1H, Ar), 7.89 (d, J = 7.8 Hz, 2H, Ar), 7.66 (t, J = 6.9 Hz, 1H, Ar), 7.59 (t, J = 7.8 Hz, 1H, Ar), 7.49 (t, J = 7.5 Hz, 2H, Ar), 7.41 (t, J = 6.9 Hz, 1H, Ar), 2.29 (s, 3H, CH3); 13C-NMR (CDCl3) δ (ppm): 192.3, 173.0, 169.3, 164.5, 153.2, 142.8, 141.3, 138.7, 136.9, 131.8, 130.6, 129.5, 125.8, 125.1, 120.1, 113.1, 108.3, 35.2; MS (EI): m/z (%): 312 [M+1]+ (43), 311 [M]+ (100), 296 (30), 270 (24), 241 (14), 214 (10), 139 (36), 111 (19), 77 (32), 51 (10).

1-(3-Chlorophenyl)-3-methylindeno[1,2-b]pyrazolo[4,3-e] pyridin-5(1H)-one (5h)

Yellow powder; yield 90% (311 mg); mp: 230-232°C; IR (KBr, cm-1): 3098, 2969, 2879, 1711, 1670, 1589, 1560, 1482, 1435, 1316, 1243, 1188, 1089, 1007, 947, 846, 764, 726, 676, 593; 1H-NMR (CDCl3) δ (ppm): 8.44 (s, 1H, Ar), 8.29 (d, J = 8.4 Hz, 1H, Ar), 8.04 (d, J = 7.5 Hz, 1H, Ar), 7.87 (d, J = 7.5 Hz, 1H, Ar), 7.69 (t, J = 7.8 Hz, 1H, Ar), 7.67 (t, J = 6.9 Hz, 1H, Ar), 7.51 (t, J = 7.5 Hz, 1H, Ar), 7.48 (s, 1H, Ar), 7.36 (d, J = 7.8 Hz, 1H, Ar), 2.29 (s, 3H, CH3); 13C-NMR (CDCl3) δ (ppm): 198.6, 181.2, 180.9, 169.0, 167.4, 166.2, 163.6, 162.9, 162.8, 151.8, 145.6, 140.3, 134.8, 134.7, 131.1, 128.9, 126.7, 121.6, 119.4, 11.9; MS (EI): m/z (%): 347 [M+2]+ (2), 345 [M]+ (4), 327 (22), 311 (100), 296 (20), 270 (15), 241 (10), 139 (30), 111 (15), 77 (17) and HRMS (ESI): calcd. for C20H12ClN3O [M]+ 345.0669; found: 345.0699.

1-(4-Chlorophenyl)-3-methylindeno[1,2-b]pyrazolo[4,3-e] pyridin-5(1H)-one (5i)

Yellow solid; yield 94% (324 mg); mp: 221-223°C; IR (KBr, cm-1): 3089, 2929, 1721, 1678, 1581, 1562, 1488, 1318, 1244, 1189, 1087, 945, 847, 765, 729, 596; 1H-NMR (CDCl3) δ (ppm): 8.84 (s, 1H, Ar), 8.14 (d, J = 8.1 Hz, 1H, Ar), 7.82 (t, J = 8.1 Hz, 1H, Ar), 7.64 (d, J = 8.1 Hz, 1H, Ar), 7.52 (t, J = 8.1 Hz, 1H, Ar), 7.36 (d, J = 7.8 Hz, 2H, Ar), 7.03 (d, J = 7.2 Hz, 2H, Ar), 2.50 (s, 3H, CH3); 13C-NMR (CDCl3) δ (ppm): 202.1, 184.9, 182.1, 178.4, 177.0, 175.9, 175.0, 149.9, 144.9, 140.1, 128.4, 128.3, 128.1, 125.1, 122.7, 120.6, 113.2, 35.2; MS (EI): m/z (%): 347 [M+2]+ (1), 345 [M]+ (2), 311 (11), 298 (8), 269 (5), 139 (100), 111 (40), 84 (16) and HRMS (ESI): calcd. for C20H12ClN3O [M]+ 345.0669; found: 345.0601.

3 Results and discussion

We earlier found that the reactions of arylglyoxals 1 with 3-methyl-1-phenyl-1H-pyrazol-5-amine (2) and cyclic 1,3-dicarbonyl compounds 3 carried out under catalyst-free conditions in H2O/EtOH at 80°C afforded 4-aroyl--pyrazolo[3,4-b]pyridine derivatives 4a-h by a one-pot, three-component reaction in excellent yields [23]. However, it was found that the same reaction in the presence of TPAB as a homogeneous catalyst in H2O/acetone at 80°C gave pyrazolopyridines 5a, 5g-i and pyrazoloquinolines 5b-f as final products in high yields due to unexpected dearoylation occurrence, with no sign of the formation of any 4-aroyl-pyrazolo[3,4-b]pyridine derivatives 4a-h formation (Scheme 1).

Scheme 1
Scheme 1

Synthesis of pyrazolopyridines and pyrazoloquinolines 5a-i.

Citation: Green Processing and Synthesis 8, 1; 10.1515/gps-2019-0022

The reaction of 4-bromophenylglyoxal monohydrate (1b), 3-methyl-1-phenyl-1H-pyrazol-5-amine (2a) and dimedone (3d) in 1:1:1 molar ratio using several catalysts, was chosen as a model reaction (Scheme 1). For optimization, the model reaction was carried out using various solvents, catalysts and reaction times as indicated in Table 1. Consequently, the highest yield (97%) was obtained, using TPAB as catalyst and H2O/acetone (1:2) as solvent, at 80°C (entry 26). The arylglyoxals 1a-i and the 3-methyl-1-aryl-1H-pyrazole-5-amines 2a-c were prepared according to the literature methods [24] and [25] respectively.

Table 1

Model reaction for the synthesis of compound 5d.

article image

EntrySolventCatalyst (20 mol%)Temperature (°C)Yield (%)a
1H2ONo catalystRT-RefluxN.R.
2H2Op-TSART-RefluxN.R.
3H2OAlginate sodiumRT-RefluxN.R.
4H2OL-cysteineRT-RefluxN.R.
5H2OL-prolineRT-RefluxN.R.
6H2OTPABRT-RefluxTrace
7EtOHp-TSART-RefluxN.R.
8EtOHAlginate sodiumRT-RefluxN.R.
9EtOHL-cysteineRT-RefluxN.R.
10EtOHL-prolineRT-RefluxN.R.
11EtOHTPABRT-RefluxTrace
12Acetonep-TSART-RefluxN.R.
13AcetoneAlginate sodiumRT-RefluxN.R.
14AcetoneL-cysteineRT-RefluxN.R.
15AcetoneL-prolineRT-RefluxN.R.
16AcetoneTPABRT-RefluxTrace
17H2O/EtOH (1:2)p-TSART-RefluxN.R.
18H2O/EtOH (1:2)Alginate sodiumRT-RefluxN.R.
19H2O/EtOH (1:2)L-cysteineRT-RefluxN.R.
20H2O/EtOH (1:2)L-prolineRT-RefluxN.R.
21H2O/EtOH (1:2)TPABRT-Reflux12
22H2O/Acetone (1:2)p-TSART-RefluxN.R.
23H2O/Acetone (1:2)Alginate sodiumRT-RefluxN.R.
24H2O/Acetone (1:2)L-cysteineRT-RefluxTrace
25H2O/Acetone (1:2)L-prolineRT-RefluxN.R.
26H2O/Acetone (1:2)TPAB80°C97b

aIsolated yield.

bThe bold type (entry 26) refers to the best reaction conditions.

After optimizing the reaction conditions, the scope of this reaction was examined with a series of electron rich and electron deficient arylglyoxals and various cyclic 1,3-dicarbonyl compounds [such as cyclopentane-1,3-dione (3a), cyclohexane-1,3-dione (3b), 4,4-dimethylcyclohexane-1,3-dione (3c), dimedone (3d) and indane-1,3-dione (3e)] to form a series of corresponding pyrazolopyridines and pyrazoloquinolines. The reaction times, melting points and yields of all products are summarized in Table 2. It should be mentioned that the reaction with 4-nitroarylglyoxal (1i) gave 4i as a final product with no sign of corresponding dearoylation product 5d formation.

Table 2

The reaction condition, melting points and yields of products 5a-i.

Entry ProductReaction time (h)M.p. (°C)Yield (%)
1

article image

3213-21696
2

article image

4126-12890
3

article image

4167-16992
4

article image

3163-16597
5

article image

3148-15098
6

article image

3144-14695
7

article image

3245-24791
8

article image

3230-23290
9

article image

4221-22394

The proposed mechanism of this reaction involves the initial Knoevenagel condenstation of arylglyoxals 1 with cyclic 1,3-dicarbonyl compounds 3 to form the corresponding intermediate as shown in Scheme 2. Following the Michael addition of 3-methyl-1-aryl-1H-pyrazol-5-one 2 to this intermediate will form the desired pyrazolopyridine and pyazoloquinoline derivatives through intermolecular cyclization, dearoylation and autoxidation. There is no report on TPAB acting as dearoylating agent in the literature.

Scheme 2
Scheme 2

A plausible mechanistic pathway for the formation of 5.

Citation: Green Processing and Synthesis 8, 1; 10.1515/gps-2019-0022

Isolation and identification of benzoic acid and 3,4-dimethoxybenzoeic acid from the literature in the case of 5a and 5g was accomplished to confirm the dearoylation step, as the melting points, TLC, FT-IR, 1H and 13C-NMR of both acids were identical with those of the authentic samples.

The structures of all products were characterized by their spectral data for new compounds or by comparison with those of authentic samples, in the case of known products.

As an important factor, the recyclability of catalyst (TPAB) was also investigated for synthesis of compound 5d.

The catalyst was recovered and reused for four times to show no significant loss on catalytic performance of TPAB as shown in Figure 1.

Figure 1
Figure 1

Reusability of TPAB for the synthesis of 5d.

Citation: Green Processing and Synthesis 8, 1; 10.1515/gps-2019-0022

4 Conclusions

Synthesis of a new series of pyrazolopyridines and pyrazoloquinolines was reported using a one-pot, three-component procedure in the presence of TPAB as a catalyst. The proposed procedure provides a new synthetic route for synthesis of pyrazolopyridine and pyrazoloquinoline derivatives, which may have pharmaceutical and biological applications. High yields, using green solvent, easily available starting materials, operational simplicity and the recoverable catalyst are some of the advantages of our procedure.

Acknowledgements

The authors gratefully acknowledge the financial support from Urmia University. We thank Professor R.H. Prager from Flinders University of Australia for proof-reading of this article.

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    Poursattar Marjani A., Khalafy J., Chitan M., Mahmoodi S., Microwave-assisted synthesis of acridine-1,8(2H5H-diones via a one-pot, three component reaction. Iran J. Chem. Chem. Eng., 2017, 36, 1-6.

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    Poursattar Marjani A., Khalafy J., Haghi A., An efficient route for the synthesis of 11-aroyldiindeno[1,2-b2′,1′-e]pyridine-10,12-diones. J. Heterocycl. Chem., 2017, 54, 3294-3298.

    • Crossref
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    Poursattar Marjani A., Taghartapeh M.R., Soltani A.R., Khalafy J., Kanani Y., Molecular structures, hirshfeld surface analysis, and spectroscopic properties of 6,8-dimethyl-3-(4-chlorophenyl)-7-oxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H-one and 6,8-dimethyl-3-(4-chlorophenyl)-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-one. J. Struct. Chem., 2017, 58, 1332-1340.

    • Crossref
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    Poursattar Marjani A., Abdollahi S., Ezzati M., Nemati‐Kande E., A facile synthesis of xanthene‐1,8(2H‐dione derivatives by using tetrapropylammonium bromide as catalyst. J. Heterocycl. Chem., 2018, 55, 1324-1330.

    • Crossref
    • Export Citation
  • [17]

    Ezzati M., Khalafy J., Poursattar Marjani A., Prager R.H., An efficient one-pot, four-component synthesis of pyrazolo[3,4-b] pyridines catalyzed by tetrapropylammonium bromide (TPAB) in water. Aust. J. Chem., 2018, 71, 435-441.

    • Crossref
    • Export Citation
  • [18]

    Poursattar Marjani A., Ebrahimi Saatluo B., Nouri F., An efficient synthesis of 4H-chromene derivatives by a one-pot, three-component reaction. Iran J. Chem. Chem. Eng., 2018, 1, 149-157.

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    Poursattar Marjani A., Khalafy J., Farajollahi A., Synthesis of ethyl 2‐amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c] quinoline‐3‐carboxylates by a one‐pot, three‐component reaction in the presence of TPAB. J. Heterocycl. Chem., 2019, 56, 268-274.

    • Crossref
    • Export Citation
  • [20]

    Poursattar Marjani A., Khalafy J., Majidi Arlan F., Eyni E., A simple protocol for the green synthesis of a new series of pyrimido[4,5-b][1,6]naphthyridines in the presence of silver nanoparticles (AgNPs). ARKIVOC., 2019, v, 1-9.

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    Dzvinchuk I.B., Tolmachova N.A., Chernega A.N., Lozinskii M.O., Aromatization with dearylation on Hantzsch cyclocondensation of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[NC]dinucleophiles. Chem. Heterocycl. Comp., 2009, 45, 194-200.

    • Crossref
    • Export Citation
  • [22]

    Sumesh R.V., Muthu M., Almansour A.I., Kumar R.S., Arumugam N., Athimoolam S., et al., Multicomponent dipolar cycloaddition strategy: combinatorial synthesis of novel spiro-tethered pyrazolo[3,4-b]quinoline hybrid heterocycles. ACS Comb. Sci., 2016, 18, 262-270.

    • Crossref
    • PubMed
    • Export Citation
  • [23]

    Ezzati M., Khalafy J., Poursattar Marjani A., Prager R.H., The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions. Tetrahedron, 2017, 73, 6587-6596.

    • Crossref
    • Export Citation
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    Riley H.A., Gray A.R. In: Blatt A.H. (Ed.), Organic Syntheses. John Wiley & Sons, New York, 1943, Vol. II, p 509.

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    Ganesan A., Heathcock C.H., Synthesis of unsymmetrical pyrazines by reaction of an oxadiazinone with enamines. J. Org. Chem., 1993, 58, 6155-6157.

    • Crossref
    • Export Citation

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    Poursattar Marjani A., Khalafy J., Mahmoodi S., A simple one-pot synthesis of new 9-aroyl-3,4,6,7,9,10-hexahydro-1,8(2H5H-acridinediones. ARKIVOC, 2016, iii, 262-270.

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    Poursattar Marjani A., Khalafy J., Chitan M., Mahmoodi S., Microwave-assisted synthesis of acridine-1,8(2H5H-diones via a one-pot, three component reaction. Iran J. Chem. Chem. Eng., 2017, 36, 1-6.

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    Poursattar Marjani A., Khalafy J., Haghi A., An efficient route for the synthesis of 11-aroyldiindeno[1,2-b2′,1′-e]pyridine-10,12-diones. J. Heterocycl. Chem., 2017, 54, 3294-3298.

    • Crossref
    • Export Citation
  • [15]

    Poursattar Marjani A., Taghartapeh M.R., Soltani A.R., Khalafy J., Kanani Y., Molecular structures, hirshfeld surface analysis, and spectroscopic properties of 6,8-dimethyl-3-(4-chlorophenyl)-7-oxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H-one and 6,8-dimethyl-3-(4-chlorophenyl)-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-one. J. Struct. Chem., 2017, 58, 1332-1340.

    • Crossref
    • Export Citation
  • [16]

    Poursattar Marjani A., Abdollahi S., Ezzati M., Nemati‐Kande E., A facile synthesis of xanthene‐1,8(2H‐dione derivatives by using tetrapropylammonium bromide as catalyst. J. Heterocycl. Chem., 2018, 55, 1324-1330.

    • Crossref
    • Export Citation
  • [17]

    Ezzati M., Khalafy J., Poursattar Marjani A., Prager R.H., An efficient one-pot, four-component synthesis of pyrazolo[3,4-b] pyridines catalyzed by tetrapropylammonium bromide (TPAB) in water. Aust. J. Chem., 2018, 71, 435-441.

    • Crossref
    • Export Citation
  • [18]

    Poursattar Marjani A., Ebrahimi Saatluo B., Nouri F., An efficient synthesis of 4H-chromene derivatives by a one-pot, three-component reaction. Iran J. Chem. Chem. Eng., 2018, 1, 149-157.

  • [19]

    Poursattar Marjani A., Khalafy J., Farajollahi A., Synthesis of ethyl 2‐amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c] quinoline‐3‐carboxylates by a one‐pot, three‐component reaction in the presence of TPAB. J. Heterocycl. Chem., 2019, 56, 268-274.

    • Crossref
    • Export Citation
  • [20]

    Poursattar Marjani A., Khalafy J., Majidi Arlan F., Eyni E., A simple protocol for the green synthesis of a new series of pyrimido[4,5-b][1,6]naphthyridines in the presence of silver nanoparticles (AgNPs). ARKIVOC., 2019, v, 1-9.

  • [21]

    Dzvinchuk I.B., Tolmachova N.A., Chernega A.N., Lozinskii M.O., Aromatization with dearylation on Hantzsch cyclocondensation of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[NC]dinucleophiles. Chem. Heterocycl. Comp., 2009, 45, 194-200.

    • Crossref
    • Export Citation
  • [22]

    Sumesh R.V., Muthu M., Almansour A.I., Kumar R.S., Arumugam N., Athimoolam S., et al., Multicomponent dipolar cycloaddition strategy: combinatorial synthesis of novel spiro-tethered pyrazolo[3,4-b]quinoline hybrid heterocycles. ACS Comb. Sci., 2016, 18, 262-270.

    • Crossref
    • PubMed
    • Export Citation
  • [23]

    Ezzati M., Khalafy J., Poursattar Marjani A., Prager R.H., The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions. Tetrahedron, 2017, 73, 6587-6596.

    • Crossref
    • Export Citation
  • [24]

    Riley H.A., Gray A.R. In: Blatt A.H. (Ed.), Organic Syntheses. John Wiley & Sons, New York, 1943, Vol. II, p 509.

  • [25]

    Ganesan A., Heathcock C.H., Synthesis of unsymmetrical pyrazines by reaction of an oxadiazinone with enamines. J. Org. Chem., 1993, 58, 6155-6157.

    • Crossref
    • Export Citation
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