Home Physical Sciences Diastereoselective synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] via visible light catalyzed cyclodimerization of 3-phenacylideneoxindoles
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Diastereoselective synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] via visible light catalyzed cyclodimerization of 3-phenacylideneoxindoles

  • Yan-Hong Jiang , Ren-Yin Yang , Jing Sun and Chao-Guo Yan EMAIL logo
Published/Copyright: May 13, 2016
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 22 Issue 3

Abstract

A simple synthetic protocol was developed for the efficient synthesis of functionalized dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] with high diastereoselectivity. The reaction proceeds by cyclodimerization reaction of 3-phenacylideneoxindoles in the presence of a catalytic amount of photosensitizer Ru(bpy3)Cl2 and visible light.

Keywords: cyclodimerization; diastereoselectivity; dispirocyclobutane-3,3′-bisoxindole; spirooxindole; visible light

Introduction

The spirooxindole core is a privileged heterocyclic ring system that is present in a large number of bioactive naturally occurring alkaloids and medicinally relevant compounds [1, 2]. The past few years have witnessed the explosive studies of the synthetic approaches to versatile spirooxindole systems [3–5], especially based on multicomponent reactions and catalytic asymmetric reactions [6]. In particular, the dispirocyclohexane-3,3′-bisoxindoles [7–10] and dispirocyclopentane-3,3′-bisoxindoles [11–19] have attracted much attention. By contrast, the reports about the construction of the corresponding dispirocyclobutane-3,3′-bisoxindoles [20, 21] and dispirocyclopropane-3,3′-bisoxindoles are rare [22, 23]. In continuation of our work to explore efficient synthetic methodology for diverse heterocyclic spirooxindoles [24–31], here we wish to report diastereoselective cyclodimerization of 3-phenacylideneoxindoles to functionalized dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines].

Results and discussion

Recently, Xiao and coworkers [32] have developed a catalytic tandem reaction of dihydroisoquinoline ester with N-phenylmaleimide for the synthesis of biologically important pyrrolo[2,1-a]isoquinolines (Equation 1 in Scheme 1). In order to further explore the synthetic application of this strategy for diverse heterocyclic systems, we attempted to use 3-phenacylideneoxindole 1a in place of N-phenylmaleimide in this reaction for the expected rapid and efficient access to spiro[indoline-3,1′-pyrrolo[2,1-a]isoquinoline] derivatives (Scheme 1). However, the reaction afforded the functionalized dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline] 2a instead and the dihydroisoquinoline ester did not react. A literature survey showed that there are only two reported examples about the construction of dispiro[indoline-cyclobutane-indoline] skeleton [20, 21]. Here, we provide additional examples of convenient synthesis of dispiro[indoline-3,1″-cyclobutane-2′,3″-indolines] by the cyclodimerization reaction of 3-phenacylideneoxindoles.

Scheme 1 Visible light catalyzed cycloaddition reactions.
Scheme 1

Visible light catalyzed cycloaddition reactions.

At first, our attention turned to optimizing the reaction conditions of cyclodimerization of 3-phenacylideneoxindoles on the basis of the procedure reported by Xiao and colleagues. Without using the photosensitizer Ru(bpy3)Cl2, and in the absence of visible light, no reaction was observed. After addition of photosensitizer Ru(bpy3)Cl2 and in the presence of visible light, the reaction in CH2Cl2, MeOH, EtOH, DMF, CH3CN afforded the expected product 2a in 10%, 61%, 64%, 75% and 90% yields, respectively. The reaction in anhydrous acetonitrile not only gave the highest yield of product, but also afforded very pure product after simple filtration and no further purification by chromatography was needed.

Under the established reaction conditions, various 3-phenacylideneoxindoles were subjected to this reaction. The products 2a–l were obtained with yields in the range of 80–96% (Scheme 2). The substituents on the substrates 1a–l show little effect on the yields. The structures of the dispirooxindoles 2a–l were fully characterized by IR, HRMS, 1H NMR and 13C NMR spectra. Because the four carbon atoms of the cyclobutane moiety in 2a–l are chiral, there are eight possible disatereoisomers for these compounds. However, the 1H NMR and 13C NMR spectra are fully consistent with the presence of a single diastereomer in each case. For an example, the 1H NMR spectrum of compound 2b displays a singlet at 2.29 ppm for two methyl groups.

Scheme 2 Synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] 2a-l.
Scheme 2

Synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] 2a-l.

The benzyl groups display two doublets at 4.79 and 4.31 ppm with geminal coupling constant J = 15.6 Hz. In order to determine the relative configuration of the dispirooxindoles, the single crystal structures of compounds 2f and 2g were determined by X-ray diffraction method (Figures 1 and 2). It can be seen that the two molecules have same configuration, in which the two oxindole moieties are in trans-configuration and the two benzoyl groups are also in trans-configuration. Additionally, the 1,2-phenylene group of the oxindole moiety is in the cis-position to the nearby benzoyl group. It has been known previously that the 1,2-phenylene fragment of the oxindole moiety and the benzoyl group exist in the cis-arrangement in the 3-phenacylideneoxindoles [33, 34]. Thus, this cis-configuration of the substrate is retained during the cyclodimerization reaction. It can be concluded that the reaction obeyes the catalytic cycle proposed by Xiao for similar visible light catalyzed [2+2] cycloaddition reaction of (E)-ethyl 2-(2-oxoindolin-3-ylidene)acetates [21].

Figure 1 Single crystal structure of compound 2f.
Figure 1

Single crystal structure of compound 2f.

Figure 2 Single crystal structure of compound 2g.
Figure 2

Single crystal structure of compound 2g.

Conclusion

An efficient synthetic protocol for functionalized dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] by the visible light catalyzed cyclodimerization reaction of 3-phenacylideneoxindoles in acetonitrile at room temperature has been developed. This diastereoselective reaction uses readily available substrates, proceeds under mild conditions and requires simple separation process.

Experimental

The catalyst Ru(bpy3)Cl2·6H2O was purchased from Amquar Biology. Acetonitrile was dried with potassium carbonate before use. All reactions were carried out under ambient atmosphere and monitored by TLC. Melting points were taken on a hot-plate microscope apparatus. IR spectra were obtained on a Bruker Tensor 27 spectrometer using KBr discs. NMR spectra were recorded with a Varian 400 spectrometer with CDCl3 as solvent and TMS as internal standard (400 MHz, and 100 MHz for 1H NMR and 13C NMR spectra, respectively). Electrospray ionization- high resolution-mass spectra (ESI-HR-MS) were obtained with a Bruker MicroTOF spectrometer. X-ray diffraction data were collected on a Bruker Smart APEX-2 CCD diffractometer.

General procedure for cyclodimerization of 3-phenacylideneoxindoles

3-Phenacylideneoxindole 1a–l (0.3 mmol) and Ru(bpy3)Cl2·6H2O (3 mol%) was dissolved in dry acetonitrile (10.0 mL), and the solution was irradiated with 36 W white light for about 12 h in ambient atmosphere at room temperature. The resulting precipitate was collected by filtration and washed with cold acetonitrile to give analytically pure product 2a–l.

3′,4′-Dibenzoyl-1,1″-dibenzyldispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2a)

White solid; yield 90%; mp 176–178°C; 1H NMR: δ 7.76 (m, 4H, ArH), 7.71 (m, 2H, ArH), 7.38 (t, J = 7.6Hz, 2H, ArH), 7.23 (m, 4H, ArH), 7.04–6.96 (m, 5H, ArH), 6.94–6.88 (m, 7H, ArH), 6.55 (m, 4H, ArH), 6.40 (t, J = 7.2 Hz, 2H, ArH), 5.83 (s, 2H, CH), 4.81 (d, J = 16.0 Hz, 2H, CH), 4.27 (d, J = 16.0 Hz, 2H, CH); 13C NMR: δ 195.7, 173.2, 142.1, 135.5, 135.1, 133.2, 128.8, 128.7, 128.6, 128.4, 128.3, 127.2, 126.7, 122.8, 121.5, 108.1, 55.6, 43.7, 43.0; IR: υ 3053, 1715, 1680, 1604, 1487, 1464, 1354, 1327, 1235, 1215, 1174, 1108, 1087, 1044, 1027, 1004, 931, 880, 794 cm-1. ESI-HR-MS. Calcd. for C46H34N2NaO4 ([M+Na]+): m/z 701.2411. Found: m/z 701.2400.

1,1″-Dibenzyl-3′,4′-bis(4-methylbenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2b)

White solid; yield 82%; mp 170–172°C; 1H NMR: δ 7.73 (m, 2H, ArH), 7.68 (t, J = 7.6 Hz, 4H, ArH), 7.06–6.98 (m, 8H, ArH), 6.96–6.90 (m, 6H, ArH), 6.59 (d, J = 7.6Hz, 2H, ArH), 6.43 (d, J = 7.6 Hz, 2H, ArH), 5.82 (s, 2H, CH), 4.79 (d, J = 15.6 Hz, 2H, CH), 4.31 (d, J = 15.6 Hz, 2H, CH), 2.29 (s, 6H, CH3); 13C NMR: δ 195.2, 173.2, 144.0, 142.1, 135.2, 133.0, 128.8, 128.7, 128.4, 128.3, 127.2, 126.7, 123.0, 121.4, 108.1, 56.7, 43.7, 42.7, 21.6; IR: υ 3028, 2919, 1706, 1672, 1607, 1487, 1464, 1406, 1354, 1301, 1240, 1181, 1108, 1037, 1003, 932, 883, 833, 792 cm-1. ESI-HR-MS. Calcd. for C48H38N2NaO4 ([M+Na]+): m/z 729.2724. Found: m/z 729.2714.

1,1″-Dibenzyl-3′,4′-bis(4-methoxybenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2c)

White solid; yield 80%; mp 168–170°C; 1H NMR: δ 7.78 (m, 2H, ArH), 7.76 (m, 3H, ArH), 7.73 (m, 1H, ArH), 7.06–6.99 (m, 4H, ArH), 6.97–6.91 (m, 6H, ArH), 6.72 (m, 2H, ArH), 6.70 (m, 2H, ArH), 6.60 (d, J = 7.2 Hz, 2H, ArH), 6.44 (m, 2H, ArH), 5.80 (s, 2H, CH), 4.80 (d, J = 15.6 Hz, 2H, CH), 4.33 (d, J = 15.6 Hz, 2H, CH), 3.77 (s, 6H, CH3); 13C NMR: δ 193.9, 173.3, 163.5, 142.1, 135.2, 130.6, 128.8, 128.7, 128.6, 118.4, 127.2, 126.7, 123.0, 121.4, 113.8, 108.1, 56.8, 55.3, 43.4, 42.5; IR: υ 2932, 2839, 1712, 1664, 1604, 1572, 1512, 1487, 1462, 1420, 1357, 1319, 1261, 1239, 1174, 1110, 994, 931, 884, 847, 793 cm-1. ESI-HR-MS. Calcd. for C48H38N2NaO6 ([M+Na]+): m/z 761.2622. Found: m/z 761.2615.

1,1″-Dibenzyl-5,5″-dimethyl-3′,4′-bis(4-methylbenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2d)

White solid; yield 89%; mp 195–197°C; 1H NMR: δ 7.69 (d, J = 7.2 Hz, 4H, ArH), 7.53 (s, 2H, ArH), 7.03 (m, 6H, ArH), 6.93 (t, J = 7.6 Hz, 4H, ArH), 6.77 (m, 2H, ArH), 6.59 (m, 4H, ArH), 6.27 (d, J = 8.0 Hz, 2H, ArH), 5.78 (s, 2H, CH), 4.77 (d, J = 16.0 Hz, 2H, CH), 4.30 (d, J = 16.0 Hz, 2H, CH), 2.30 (s, 6H, CH3), 2.28 (s, 6H, CH3); 13C NMR: δ 195.4, 173.1, 143.8, 139.7, 135.4, 133.1, 130.7, 129.5, 129.3, 128.8, 128.4, 128.3, 127.1, 126.7, 123.0, 107.6, 56.8, 43.7, 42.8, 21.6, 21.1; IR: υ 2917, 1714, 1677, 1641, 1570, 1495, 1415, 1349, 1321, 1249, 1184, 1092, 1050, 1022, 938, 812 cm-1. ESI-HR-MS. Calcd. for C50H42N2NaO4 ([M+Na]+): m/z 757.3037. Found: m/z 757.3030.

1,1″-Dibenzyl-3′,4′-bis(4-chlorobenzoyl)-5,5″-dimethyldispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2e)

White solid; yield 86%; mp 178–180°C; 1H NMR: δ 7.71 (m, 2H, ArH), 7.69 (m, 2H, ArH), 7.47 (brs, 2H, ArH), 7.21 (m, 2H, ArH), 7.19 (m, 2H, ArH), 7.07 (m, 2H, ArH), 6.97 (m, 4H, ArH), 6.81 (t, J = 7.6 Hz, 2H, ArH), 6.61 (d, J = 7.2 Hz, 2H, ArH), 6.33 (d, J = 8.0 Hz, 2H, ArH), 5.72 (s, 2H, CH), 4.75 (d, J = 15.6 Hz, 2H, CH), 4.33 (d, J = 15.6 Hz, 2H, CH), 2.28 (s, 6H, CH3); 13C NMR: δ 194.6, 172.9, 139.7, 139.6, 135.2, 133.8, 130.9, 129.6, 129.3, 129.2, 129.1, 129.0, 128.6, 128.4, 127.3, 126.8, 122.6, 107.9, 56.6, 43.8, 43.0, 21.1; IR: υ 2916, 1716, 1684, 1644, 1589, 1493, 1431, 1403, 1348, 1312, 1249, 1199, 1176, 1095, 1048, 1009, 937, 837, 807, 787 cm-1. ESI-HR-MS. Calcd. for C48H36Cl2N2NaO4 ([M+Na]+): m/z 797.1944. Found: m/z 797.1939.

1,1″-dibutyl-3′,4′-bis(4-methoxybenzoyl)-5,5″-dimethyldispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2f)

White solid; yield 94%; mp 172–174°C; 1H NMR: δ 7.74–7.73 (m, 2H, ArH), 7.71–7.70 (m, 2H, ArH), 7.53 (brs, 2H, ArH), 6.85–6.83 (m, 2H, ArH), 6.74–6.70 (m, 4H, ArH), 6.35 (d, J = 8.0 Hz, 2H, ArH), 5.62 (s, 2H, CH), 3.75 (s, 6H, CH3), 3.51–3.44 (m, 2H, CH), 3.30–3.23 (m, 2H, CH), 1.28–1.20 (m, 4H, CH), 0.90–0.84 (m, 4H, CH), 0.70 (t, J = 8.0 Hz, 6H, CH3); 13C NMR: δ 194.3, 173.0, 163.3, 139.9, 130.5, 130.2, 129.8, 128.8, 128.7, 123.1, 113.6, 106.8, 56.4, 55.2, 43.2, 39.5, 29.0, 21.1, 19.4, 13.5; IR: υ 2968, 2933, 2874, 2844, 1701, 1668, 1600, 1572, 1514, 1493, 1422, 1359, 1315, 1266, 1217, 1196, 1172, 1109, 1025, 986, 928, 882, 848, 803 cm-1. ESI-HR-MS. Calcd. for C44H46N2NaO6 ([M+Na]+): m/z 721.3248. Found: m/z 721.3242.

1,1″-Dibenzyl-5,5″-dichloro-3′,4′-bis(4-methylbenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2g)

White solid; yield 96%; mp 194–196°C; 1H NMR: δ 7.74–7.73 (m, 2H, ArH), 7.68 (d, J = 8.4 Hz, 4H, ArH), 7.11–7.05 (m, 6H, ArH), 6.97 (m, 6H, ArH), 6.64 (d, J = 7.2 Hz, 2H, ArH), 6.33 (d, J = 8.4 Hz, 2H, ArH), 5.76 (s, 2H, CH), 4.73 (d, J = 15.6 Hz, 2H, CH), 4.37 (d, J = 15.6 Hz, 2H, CH), 2.32 (s, 6H, CH3); 13C NMR: δ 194.6, 172.6, 144.3, 140.6, 134.8, 132.8, 129.5, 129.3, 128.9, 128.5, 128.4, 127.5, 127.2, 126.8, 124.2, 109.0, 56.2, 43.9, 42.7, 21.7; IR: υ 2920, 1721, 1678, 1641, 1483, 1425, 1313, 1321, 1269, 1239, 1181, 1086, 1046, 1023, 934, 905, 815, 792 cm-1. ESI-HR-HRMS. Calcd. for C48H36Cl2N2NaO4 ([M+Na]+): m/z 797.1944. Found: m/z 797.1931.

1,1″-dibutyl-5,5″-dichloro-3′,4′-bis(4-methoxybenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2h)

White solid; yield 93%; mp 187–189°C; 1H NMR: δ 7.71 (m, 6H, ArH), 7.04 (dd, J1 = 8.4 Hz, J2 = 2.0 Hz, 2H, ArH), 6.74 (m, 4H, ArH), 6.40 (d, J = 8.4 Hz, 2H, ArH), 5.61 (s, 2H, CH), 3.77 (s, 6H, CH3), 3.53–3.47 (m, 2H, CH), 3.24 (m, 2H, CH), 1.30–1.20 (m, 4H, CH), 0.72 (t, J = 7.6 Hz, 6H, CH3); 13C NMR: δ 193.5, 172.4, 163.6, 140.8, 130.6, 129.4, 128.6, 128.4, 126.6, 124.3, 113.8, 108.1, 55.9, 55.3, 42.9, 39.7, 29.9, 19.4, 13.5; IR: υ 2970, 2934, 2845, 1707, 1665, 1602, 1572, 1514, 1482, 1424, 1344, 1316, 1268, 1236, 1172, 1106, 1025, 984, 928, 904, 849, 806 cm-1. ESI-HR-MS. Calcd. for C42H40Cl2N2NaO6 ([M+Na]+): m/z 761.2156. Found: m/z 761.2151.

3′,4′-Dibenzoyl-1,1″-dibenzyl-5,5″-difluorodispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2i)

White solid; yield 87%; mp 173–175°C; 1H NMR: δ 7.78 (m, 4H, ArH), 7.04 (dd, J1 = 8.8 Hz, J2 = 3.0 Hz, 2H, ArH), 7.43 (m, 2H, ArH), 7.28 (m, 3H, ArH), 7.25 (brs, 1H, ArH), 7.07 (m, 2H, ArH), 6.95 (m, 4H, ArH), 6.71 (td, J1 = 8.8 Hz, J2 = 3.0 Hz, 2H, ArH), 6.61 (m, 4H, ArH), 6.32 (m, 2H, ArH), 5.80 (s, 2H, CH), 4.82 (d, J = 16.0 Hz, 2H, CH), 4.31 (d, J = 16.0 Hz, 2H, CH); 13C NMR: δ 195.2, 172.8, 157.9 (d, J = 240.0 Hz), 138.2, 138.1, 135.2, 134.7, 133.4, 128.7, 128.5, 128.3, 127.5, 126.6, 124.2 (d, J = 9.0 Hz), 117.6 (d, J = 26.3 Hz), 115.4 (d, J = 23.5 Hz), 108.4 (d, J = 8.0 Hz), 56.4, 56.3, 43.9, 42.9; IR: υ 2934, 1714, 1679, 1641, 1488, 1448, 1346, 1305, 1270, 1244, 1215, 1175, 1083, 1044, 1018, 940, 880, 846, 811, 786 cm-1. ESI-HR- MS. Calcd. for C46H34F2N2NaO4 ([M+Na]+): m/z 737.2222. Found: m/z 737.2227.

1,1″-Dibutyl-5,5″-difluoro-3′,4′-bis(4-methoxybenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2j)

White solid; yield 85%; mp 160–162°C; 1H NMR δ: 7.72 (d, J = 8.8 Hz, 4H, ArH), 7.52 (dd, J1 = 8.8 Hz, J2 = 2.0 Hz, 2H, ArH), 6.81–6.73 (m, 6H, ArH), 6.40 (m, 2H, ArH), 5.63 (s, 2H, CH), 3.77 (s, 6H, CH3), 3.56–3.48 (m, 2H, CH), 3.32–3.26 (m, 2H, CH), 1.33–1.19 (m, 4H, CH), 0.72 (t, J = 7.2 Hz, 6H, CH3); 13C NMR: δ 193.5, 172.6, 163.6, 157.7 (d, J = 238.7 Hz), 138.3, 138.2, 130.6, 128.4, 124.4 (d, J = 9.1 Hz), 117.3 (d, J = 26.2 Hz), 115.1(d, J = 23.4 Hz), 113.8, 107.5 (d, J = 8.0 Hz), 55.3, 42.9, 39.7, 28.9, 19.4, 13.5; IR: υ 2958, 2869, 1722, 1696, 1655, 1601, 1571, 1491, 1451, 1420, 1348, 1313, 1267, 1167, 1133, 1110, 1020, 970, 936, 882, 834, 811 cm-1. ESI-HR-MS. Calcd. for C42H40F2N2NaO6 ([M+Na]+): m/z 729.2747. Found: m/z 729.2737.

1,1″-Dibenzyl-6,6″-dichloro-3′,4′-bis(4-methoxybenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2k)

White solid; yield 86%; mp 164–166°C; 1H NMR δ: 7.75 (m, 4H, ArH), 7.61 (d, J = 8.0 Hz, 4H, ArH), 7.09–7.06 (m, 2H, ArH), 6.97 (t, J = 7.6 Hz, 4H, ArH), 6.91 (dd, J1 = 8.0 Hz, J2 = 2.0 Hz, 2H, ArH), 6.74 (m, 4H, ArH), 6.57–6.55 (m, 4H, ArH), 6.44 (d, J = 2.0 Hz, 2H, ArH), 5.77 (s, 2H, 2CH), 4.80 (d, J = 15.6 Hz, 2H, 2CH), 4.26 (d, J = 15.6 Hz, 2H, 2CH), 3.80 (s, 6H, 2CH3); 13C NMR: δ 193.4, 173.2, 163.7, 143.3, 134.7, 134.5, 130.5, 129.6, 128.5, 128.3, 127.6, 126.6, 121.5, 121.2, 113.9, 108.8, 56.3, 55.3, 43.8, 41.8; IR: υ 3050, 2987, 1716, 1666, 1602, 1576, 1487, 1437, 1344, 1244, 1175, 1121, 1083, 1027, 987, 928, 883, 842, 812 cm-1. ESI-HR-MS. Calcd. for C48H36Cl2N2NaO4 ([M+Na]+): 829.1843. Found: m/z 829.1826.

1,1″-Dibenzyl-6,6″-dichloro-3′,4′-bis(4-chlorobenzoyl)dispiro[indoline-3,1′-cyclobutane-2′,3″-indoline]-2,2″-dione (2l)

White solid; yield 89%; mp 146–148°C; 1H NMR: δ 7.67 (d, J = 8.8 Hz, 4H, ArH), 7.54 (d, J = 8.8 Hz, 4H, ArH), 7.24–7.21 (m, 4H, ArH), 7.11–7.10 (m, 2H, ArH), 7.02–6.98 (m, 4H, ArH), 6.91 (dd, J1 = 8.0 Hz, J2 = 1.6 Hz, 2H, ArH), 6.58–6.57 (m, 4H, ArH), 6.49 (d, J = 1.6 Hz, 2H, ArH), 5.73 (s, 2H, 2CH), 4.77 (d, J = 15.6 Hz, 2H, 2CH), 4.28 (d, J = 15.6 Hz, 2H, 2CH); 13C NMR δ: 193.8, 172.9, 143.2, 140.1, 135.2, 134.3, 133.3, 129.5, 129.4, 129.1, 128.7, 128.6, 127.7, 126.7, 121.6, 120.6, 109.0, 56.1, 43.9, 42.2; IR: υ 2920, 1717, 1681, 1600, 1487, 1439, 1341, 1288, 1258, 1228, 1176, 1089, 1005, 928, 883, 836 cm-1; ESI-HR-MS. Calcd. for C46H30Cl4N2NaO4 ([M+Na]+): m/z 837.0852. Found: m/z 837.0812.

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 21172189, 21572196

Funding statement: This work was financially supported by the National Natural Science Foundation of China (Grant No. 21172189, 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We also thank the Analysis and Test Center of Yangzhou University providing instruments for analysis.

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Grant No. 21172189, 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We also thank the Analysis and Test Center of Yangzhou University providing instruments for analysis.

Supporting information:1H and 13C NMR spectra for all new compounds are available (see also the online supplementary material). Crystallographic data 2f (CCDC 1450367) and 2g (CCDC 1450368) have been deposited at the Cambridge Crystallographic Database Centre.

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Supplemental Material:

The online version of this article (DOI: 10.1515/hc-2016-0022) offers supplementary material, available to authorized users.

Received: 2016-2-2
Accepted: 2016-4-13
Published Online: 2016-5-13
Published in Print: 2016-6-1

©2016 by De Gruyter

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.

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  1. Frontmatter
  2. Research Articles
  3. TiCl2·2H2O catalyzed one-pot synthesis of highly functionalized tetrahydropiperidines and evaluation of their antimicrobial activities
  4. 2,5-Disubstituted 1,3,4-oxadiazole derivatives of chromeno[4,3-b]pyridine: synthesis and study of antimicrobial potency
  5. Catalytic synthesis and antimicrobial activity of N-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
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https://doi.org/10.1515/hc-2016-0022
Keywords for this article
cyclodimerization; diastereoselectivity; dispirocyclobutane-3,3′-bisoxindole; spirooxindole; visible light
Creative Commons
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Articles in the same Issue

  1. Frontmatter
  2. Research Articles
  3. TiCl2·2H2O catalyzed one-pot synthesis of highly functionalized tetrahydropiperidines and evaluation of their antimicrobial activities
  4. 2,5-Disubstituted 1,3,4-oxadiazole derivatives of chromeno[4,3-b]pyridine: synthesis and study of antimicrobial potency
  5. Catalytic synthesis and antimicrobial activity of N-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
  6. Benzo[e][1,2,4]triazino[2,3-c][1,2,3]triazin-2-ones electro-deficient heterocyclic compounds with promising anticancer activity
  7. Synthesis and biological activity studies of some new hybrid compounds derived from antipyrine
  8. Diastereoselective synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] via visible light catalyzed cyclodimerization of 3-phenacylideneoxindoles
  9. Synthesis of 6-alkylsulfanyl-1,4-dihydropyridines as potential multidrug resistance modulators
  10. Lactic acid-catalyzed fusion of ninhydrin and enamines for the solvent-free synthesis of hexahydroindeno[1,2-b]indole-9,10-diones
  11. Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes
  12. A direct synthetic route to fused tricyclic quinolones from 2,3-diaminoquinolin-4(1H)one
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