Synthesis of spiro[pyrazole-4,8′-pyrazolo [3,4-f]quinolin]-5(1H)-ones by the reaction of aldehydes with 1H-indazol-6-amine and 1H-pyrazol-5(4H)-one

Fang Dong; Xiang-Shan Wang

doi:10.1515/hc-2016-0116

Artikel Open Access

Synthesis of spiro[pyrazole-4,8′-pyrazolo [3,4-f]quinolin]-5(1H)-ones by the reaction of aldehydes with 1H-indazol-6-amine and 1H-pyrazol-5(4H)-one

Fang Dong und Xiang-Shan Wang

Veröffentlicht/Copyright: 24. September 2016

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Abstract

A four-component reaction including two equivalents of aldehyde, 1H-indazol-6-amine and 1H-pyrazol-5(4H)-one proceeds smoothly to afford a series of spiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-ones in high yields under catalyst-free conditions.

Keywords: 1H-indazol-6-amine; 1H-pyrazol-5(4H)-one; pyrazoloquinoline; spiro

Introduction

Due to unique antimalarial activity, quinoline derivatives have received considerable attention in recent years [1], [2], [3] and some of them including chloroquine [4] and plasmoquine [5] (Figure 1) are clinical drugs to treat malaria. Pyrazole exhibits a wide range of biological applications. A typical example is analgesic and antipyretic drug antipyrine [6]. Pyrazole fused quinoline (pyrazoloquinoline) is also a useful heterocycle whose derivatives show various bioactivities including antimalarial [7], analgesic [8], antipsychotic [9], and antimicrobial activities [10]. Many procedures have been reported to synthesize these active compounds in the past few years [11], [12], [13], [14].

Figure 1

The marketed drugs containing pyrazole or quinoline.

In our previous paper, the reactions of aldehyde, 1H-indazol-6-amine and 3-phenylisoxazol-5(4H)-one were performed in refluxing EtOH, giving spiro[isoxazole-4,8′-pyrazolo[3,4-f]quino-lin]-5-ones or ring-opening products of pyrazoloquinolines depending on the activity of the aldehyde. In view of the importance of pyrazole, the aldehyde 1 was allowed to react with 1H-indazol-6-amine 2 and 1H-pyrazol-5(4H)-one 3 under similar reaction conditions (Scheme 1). This reaction gave exclusively spiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-ones 4 regardless of the type of substituents on the substrates. This report describes a continuation of our research devoted to the development of new methods for the preparation of heterocycles containing nitrogen atoms under catalyst-free conditions [15], [16], [17], [18].

Scheme 1

The synthetic route for the products 4.

Results and discussion

The initial reaction involved two equivalents of 4-nitrobenzaldehyde (1a, 2.0 mmol), 1H-indazol-6-amine (2, 1.0 mmol) and 1,3-dimethyl-1H-pyrazol-5(4H)-one (3, 1.0 mmol) in refluxing EtOH (Scheme 1). This reaction furnished 1,3-dimethyl-7′,9′-bis(2-nitrophenyl)-1′,6′,7′,9′-tetrahydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4a) in an 89% yield. This model reaction was conducted in various solvents including THF, MeOH, EtOH, dioxane, toluene, and DMF. It was found that under catalyst-free conditions the use of EtOH is optimal.

Subsequently, various aldehydes 1 were allowed to react with 2 and 3 in EtOH under reflux conditions. All products 4a–n were obtained in 84%–91% yields. The presence of electron-donating (alkyl) or electron-withdrawing (halide, nitro, and cyano) group on the substrates does not affect the high efficiency of the reaction.

Conclusion

The efficient synthesis of spiro[pyrazole-4,8′-pyrazolo [3,4-f]quinolin]-5(1H)-one derivatives 4 by the reaction of two equivalents of aldehyde 1 with 1H-indazol-6-amine 2 and 1H-pyrazol-5(4H)-one 3 is described. The four-component reaction proceeds smoothly in refluxing EtOH in the absence of any catalysts.

Experimental

Melting points were determined in open capillaries and are uncorrected. IR spectra were recorded on a Tensor 27 spectrometer in KBr pellets. ¹H NMR spectra were obtained in DMSO-d₆ with Me₄Si as internal standard using a Bruker-400 spectrometer (400 MHz). HR-MS analyses were carried out using a Bruker-micro- TOF-Q-MS analyzer.

General procedure for the synthesis of 4

A mixture of aromatic aldehyde 1 (2.0 mmol), 1H-indazol-6-amine 2 (1.0 mmol), 1H-pyrazol-5(4H)-one 3 (112 mg, 1.0 mmol), and EtOH (10.0 mL) was stirred at reflux for 6–10 h. After the completion of the reaction as indicated by TLC analysis, the pure product 4 was obtained by simple filtration after cooling the mixture to room temperature.

1,3-Dimethyl-7′,9′-bis(4-nitrophenyl)-1′,6′,7′,9′-tetrahydro spiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4a)

Yield 89%; mp 254–255°C; ¹H NMR: δ_H 1.95 (s, 3H, CH₃), 2.71 (s, 3H, CH₃), 4.83 (s, 1H, CH), 5.09 (s, 1H, CH), 6.90 (m, 2H, ArH), 7.04 (s, 1H, NH), 7.36 (m, 1H, ArH), 7.60 (m, 3H, ArH), 7.89 (s, 1H, ArH), 7.96 (m, 1H, ArH), 8.19 (s, 1H, ArH), 8.24 (d, J=8.8 Hz, 2H, ArH), 11.27 (s, 1H, NH); IR: ν 3311, 2930, 1685, 1624, 1597, 1529, 1492, 1437, 1404, 1348, 1291, 1256, 1093, 1059, 1014, 931, 871, 859, 838, 820, 795, 719 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀N₇O₅ ([M – H]⁻): m/z 510.1520. Found: m/z 510.1537.

7′,9′-Bis(4-chlorophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetrahydro spiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4b)

Yield 91%, mp 272–274°C; ¹H NMR: δ_H 1.97 (s, 3H, CH₃), 2.71 (s, 3H, CH₃), 4.61 (s, 1H, CH), 4.90 (s, 1H, CH), 6.58 (m, 1H, ArH), 6.82 (s, 1H, NH), 6.82 (d, J=8.8 Hz, 1H, ArH), 7.10 (m, 1H, ArH), 7.14 (m, 1H, ArH), 7.35 (m, 3H, ArH), 7.42 (m, 2H, ArH), 7.53 (d, J=8.4 Hz, 1H, ArH), 7.85 (s, 1H, ArH), 11.14 (s, 1H, NH); IR: ν 3377, 3253, 3063, 2926, 1697, 1621, 1589, 1524, 1489, 1428, 1376, 1354, 1255, 1173, 1089, 1057, 1014, 968, 927, 841, 730, 706 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀Cl₂N₅O ([M – H]⁻) : m/z 488.1039. Found: m/z 488.1066.

1,3-Dimethyl-7′,9′-bis(2-nitrophenyl)-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4c)

Yield 86%; mp 226–228°C; ¹H NMR: δ_H 1.94 (s, 3H, CH₃), 2.54 (s, 3H, CH₃), 5.26 (s, 1H, CH), 5.37 (s, 1H, CH), 6.82 (d, J=8.8 Hz, 1H, ArH), 7.16 (d, J=8.0 Hz, 1H, ArH), 7.30 (s, 1H, NH), 7.47 (d, J=8.8 Hz, 2H, ArH), 7.57 (m, 4H, ArH), 7.62~7.72 (m, 2H, ArH), 8.24 (d, J=8.0 Hz, 1H, ArH), 12.56 (s, 1H, NH); IR: ν 3395, 3166, 2971, 2929, 1698, 1630, 1576, 1527, 1463, 1429, 1377, 1343, 1322, 1226, 1187, 1045, 1018, 936, 874, 862, 850, 789, 730 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀N₇O₅ ([M – H]⁻) : m/z 510.1520. Found: m/z 510.1543.

1,3-Dimethyl-7′,9′-bis(3-nitrophenyl)-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4d)

Yield 84%; mp>300°C; ¹H NMR: δ_H 2.02 (s, 3H, CH₃), 2.67 (s, 3H, CH₃), 4.83 (s, 1H, CH), 5.07 (s, 1H, CH), 6.91 (d, J=8.8 Hz, 1H, ArH), 7.06 (d, J=9.6 Hz, 2H, ArH), 7.32 (s, 1H, NH), 7.41 (m, 1H, ArH), 7.60 (d, J=9.6 Hz, 1H, ArH), 7.69 (m, 2H, ArH), 7.79 (d, J=8.0 Hz, 2H, ArH), 7.88 (s, 1H, ArH), 8.13 (m, 1H, ArH), 11.27 (s, 1H, NH); IR: ν 3419, 3309, 3084, 2927, 1695, 1623, 1600, 1531, 1498, 1438, 1373, 1351, 1258, 1225, 1075, 1056, 1001, 929, 845, 811, 798, 781, 760, 740, 715 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀N₇O₅ ([M – H]⁻): m/z 510.1520. Found: m/z 510.1526.

7′,9′-Bis(4-chloro-2-nitrophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetrahydrospiro [pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4e)

Yield 86%; mp 211–212°C; ¹H NMR: δ_H 1.93 (s, 3H, CH₃), 2.60 (s, 3H, CH₃), 5.22 (s, 1H, CH), 5.25 (s, 1H, CH), 7.16 (d, J=8.4 Hz, 2H, ArH), 7.36 (s, 1H, NH), 7.58 (m, 2H, ArH), 7.81 (m, 3H, ArH), 7.96 (d, J=2.4 Hz, 1H, ArH), 8.30 (s, 1H, ArH), 12.59 (s, 1H, NH); IR: ν 3409, 3176, 3098, 3042, 2970, 1694, 1659, 1624, 1566, 1530, 1459, 1434, 1421, 1388, 1378, 1354, 1342, 1332, 1325, 1102, 1065, 932, 894, 852, 841 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₁₈Cl₂N₇O₅ ([M – H]⁻) : m/z 578.0740. Found: m/z 578.0697.

7′,9′-Bis(5-bromo-2-nitrophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4f)

Yield 90%; mp 216–218°C; ¹H NMR: δ_H 1.92 (s, 3H, CH₃), 2.60 (s, 3H, CH₃), 5.24 (s, 1H, CH), 5.36 (s, 1H, CH), 6.82 (d, J=8.8 Hz, 1H, ArH), 7.21 (s, 1H, NH), 7.42 (s, 1H, ArH), 7.62 (m, 2H, ArH), 7.80 (m, 3H, ArH), 7.88 (s, 1H, ArH), 8.19 (d, J=8.8 Hz, 1H, ArH), 12.70 (s, 1H, NH); IR: ν 3342, 3175, 3066, 2926, 1696, 1659, 1626, 1597, 1566, 1522, 1496, 1462, 1421, 1377, 1339, 1290, 1256, 1182, 1099, 932, 875, 843 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₁₈Br₂N₇O₅ ([M – H]⁻): m/z 665.9730. Found: m/z 665.9690.

1,3-Dimethyl-7′,9′-bis(2-(trifluoromethyl)phenyl)-1′,6′,7′,9′-tetrahydrospiro [pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4g)

Yield 87%; mp 264–265°C; ¹H NMR: δ_H 1.97 (s, 3H, CH₃), 2.70 (s, 3H, CH₃), 4.76 (s, 1H, CH), 5.21 (s, 1H, CH), 6.77 (d, J=8.8 Hz, 1H, ArH), 7.07 (s, 1H, NH), 7.32 (s, 1H, ArH), 7.37 (d, J=8.0 Hz, 1H, ArH), 7.52 (m, 3H, ArH), 7.67 (m, 3H, ArH), 7.97 (s, 2H, ArH), 11.01 (s, 1H, NH); IR: ν 3297, 2921, 1709, 1669, 1625, 1595, 1513, 1497, 1437, 1378, 1344, 1310, 1291, 1258, 1157, 1135, 1061, 1038, 929, 858, 770 cm⁻¹. ESI-HR-MS. Calcd for C₂₈H₂₀F₆N₅O ([M – H]⁻ ): m/z 556.1566. Found: m/z 556.1546.

1,3-Dimethyl-7′,9′-bis(4-(trifluoromethyl)phenyl)-1′,6′,7′,9′-tetrahydrospiro [pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4h)

Yield 84%; mp 244–245°C; ¹H NMR: δ_H 1.74 (s, 3H, CH₃), 2.76 (s, 3H, CH₃), 4.65 (s, 1H, CH), 5.07 (s, 1H, CH), 7.06 (m, 3H, ArH), 7.44 (d, J=8.8 Hz, 2H, ArH), 7.59 (m, 1H, ArH), 7.69 (s, 1H, NH), 7.75 (d, J=2.4 Hz, 1H, ArH), 8.22 (s, 1H, ArH), 8.54 (s, 1H, ArH), 8.69 (s, 2H, ArH), 12.32 (s, 1H, NH); IR: ν 3196, 3083, 1715, 1633, 1604, 1550, 1524, 1470, 1447, 1380, 1346, 1239, 1202, 1135, 1092, 1072, 950, 893, 859, 825, 786 cm⁻¹; ESI-HR-MS. Calcd for C₂₈H₂₀F₆N₅O ([M – H]⁻): m/z 556.1566. Found: 556.1543.

7′,9′-bis(4-bromo-2-nitrophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetrahydrospiro [pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4i)

Yield 89%; mp 271–272°C; ¹H NMR: δ_H 2.09 (s, 3H, CH₃), 2.76 (s, 3H, CH₃), 4.06 (s, 1H, CH), 5.70 (s, 1H, CH), 6.60 (s, 3H, ArH), 7.67~7.71 (m, 1H, ArH), 7.80 (m, 2H, ArH), 7.96 (s, 1H, NH), 8.09 (m, 2H, ArH), 8.18 (d, J=8.0 Hz, 1H, ArH), 12.25 (s, 1H, NH); IR: ν 3196, 3083, 1715, 1633, 1604, 1550, 1524, 1470, 1447, 1380, 1346, 1239, 1202, 1135, 1092, 1072, 950, 893, 859, 825, 786 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₁₈Br₂N₇O₅ ([M – H]⁻): m/z 665.9730. Found m/z 665.9685.

7′,9′-Bis(4-bromophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4j)

Yield 85%; mp 272–273°C; ¹H NMR: δ_H 2.09 (s, 3H, CH₃), 2.64 (s, 3H, CH₃), 4.68 (s, 1H, CH), 4.94 (s, 1H, CH), 6.18 (s, 1H, ArH), 6.53 (s, 1H, NH), 6.75 (m, 1H, ArH), 7.07 (d, J=8.0 Hz, 1H, ArH), 7.20~7.23 (m, 2H, ArH), 7.39 (m, 4H, ArH), 7.57~7.60 (m, 1H, ArH), 7.95~7.98 (m, 1H, ArH), 12.83 (s, 1H, NH); IR: ν 3367, 3208, 2924, 1693, 1672, 1620, 1588, 1487, 1428, 1407, 1378, 1326, 1254, 1169, 1089, 1073, 1009, 926, 842, 860, 797, 756, 729, 704 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀Br₂N₅O ([M – H]⁻): m/z 576.0035. Found: m/z 576.0002.

1,3-Dimethyl-7′,9′-di-p-tolyl-1′,6′,7′,9′-tetrahydrospiro[pyrazole-4,8′-pyrazolo [3,4-f]quinolin]-5(1H)-one (4k)

Yield 84%; mp 267–268°C; ¹H NMR: δ_H 1.96 (s, 3H, CH₃), 2.30 (s, 3H, CH₃). 2.40 (s, 3H, CH₃). 2.66 (s, 3H, CH₃), 4.52 (s, 1H, CH), 4.86 (s, 1H, CH), 6.45 (d, J=8.0 Hz, 1H, ArH), 6.68 (s, 1H, NH), 6.84~6.88 (m, 2H, ArH), 6.99~7.03 (m, 1H, ArH), 7.10 (m, 1H, ArH), 7.12~7.21 (m, 4H, ArH), 7.49 (d, J=8.4 Hz, 1H, ArH), 7.80 (s, 1H, ArH), 10.85 (s, 1H, NH); IR: ν 3403, 3250, 3061, 3028, 2918, 2865, 1686, 1617, 1588, 1487, 1432, 1375, 1327, 1259, 1225, 1060, 1021, 929, 846, 801, 733, 701 cm⁻¹. HRMS (ESI, m/z): Calcd for C₂₈H₂₆N₅O [M – H]⁻ 448.2131, found 448.2122.

7′,9′-bis(4-methoxyphenyl)-1,3-dimethyl-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4l)

Yield 86%; mp 258–259°C; ¹H NMR: δ_H 1.99 (s, 3H, CH₃), 2.68 (s, 3H, CH₃), 3.69 (s, 3H, OCH₃), 3.73 (s, 3H, OCH₃), 4.53 (s, 1H, CH), 4.84 (s, 1H, CH), 6.40 (s, 1H, NH), 6.48~6.51 (m, 1H, ArH), 6.62~6.65 (m, 1H, ArH), 6.68 (s, 1H, ArH), 6.84 (d, J=2.4 Hz, 1H, ArH), 6.97 (d, J=8.8 Hz, 1H, ArH), 7.03~7.05 (m, 1H, ArH), 7.10~7.12 (m, 1H, ArH), 7.42 (d, J=8.4 Hz, 1H, ArH), 7.49 (d, J=8.4 Hz, 1H, ArH), 7.72~7.76 (m, 1H, ArH), 7.80 (s, 1H, ArH), 10.76 (s, 1H, NH); IR: ν 3412, 3234, 3038, 3004, 2956, 2927, 2838, 1686, 1618, 1584, 1512, 1489, 1462,1382, 1305, 1253, 1177, 1107, 1060, 1030, 964, 832, 803, 739, 703 cm⁻¹. ESI-HR-MS. Calcd for C₂₈H₂₆N₅O₃ ([M – H]⁻): m/z 480.2108. Found: m/z 480.2082.

7′,9′-Bis(3-bromophenyl)-1,3-dimethyl-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4m)

Yield 84%; mp 287–288°C; ¹H NMR: δ_H 1.84 (s, 3H, CH₃), 2.68 (s, 3H, CH₃), 4.52 (s, 1H, CH), 4.78 (s, 1H, CH), 6.47 (d, J=8.0 Hz, 1H, ArH), 6.53 (s, 1H, NH), 6.78 (m, 3H, ArH), 7.14 (s, 1H, ArH), 7.23 (s, 1H, ArH), 7.24 (s, 1H, ArH), 7.23 (s, 1H, ArH), 7.41 (s, 1H, ArH), 7.42 (m, 1H, ArH), 7.76 (s, 1H, ArH), 11.22 (s, 1H, NH); IR: ν 3447, 3196, 2923, 1694, 1622, 1591, 1565, 1510, 1474, 1428, 1374, 1302, 1234, 1091, 1069, 1030, 995, 925, 836, 799, 786, 754, 721 cm⁻¹. ESI-HR-MS. Calcd for C₂₆H₂₀Br₂N₅O ([M – H]⁻): m/z 576.0010. Found: m/z 576.0006.

1,3,3′-Trimethyl-7′,9′-bis(4-nitrophenyl)-1′,6′,7′,9′-tetra hydrospiro[pyrazole-4,8′-pyrazolo[3,4-f]quinolin]-5(1H)-one (4n)

Yield 89%; mp 271–272°C; ¹H NMR: δ_H 2.30 (s, 3H, CH₃), 2.40 (s, 3H, CH₃), 2.45 (s, 3H, CH₃), 5.04 (s, 1H, CH), 5.12 (s, 1H, CH), 6.74 (d, J=8.4 Hz, 2H, ArH), 7.00 (s, 1H, NH), 7.41 (d, J=8.4 Hz, 1H, ArH), 7.65 (m, 3H, ArH), 7.97 (m, 2H, ArH), 8.22 (d, J=8.8 Hz, 2H, ArH), 12.25 (s, 1H, NH); IR: ν 3396, 3082, 2934, 1704, 1618, 1604, 1604, 1513, 1470, 1428, 1377, 1345, 1263, 1224, 1153, 1107, 1012, 976, 956, 860, 810, 735, 745 cm⁻¹. ESI-HR-MS. Calcd for C₂₇H₂₂N₇O₅ ([M – H]⁻): m/z 524.1676. Found: m/z 524.1686.

Funding source: Natural Science Foundation of Jiangsu Province

Award Identifier / Grant number: 14KJA150004

Funding statement: We are grateful to the Major Natural Science Foundation of Jiangsu Province (14KJA150004) and the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support

Acknowledgments

We are grateful to the Major Natural Science Foundation of Jiangsu Province (14KJA150004) and the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

References

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Received: 2016-7-12

Accepted: 2016-7-30

Published Online: 2016-9-24

Published in Print: 2016-10-1

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Artikel in diesem Heft

https://doi.org/10.1515/hc-2016-0116

Schlagwörter für diesen Artikel

1H-indazol-6-amine; 1H-pyrazol-5(4H)-one; pyrazoloquinoline; spiro

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