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Article

Synthesis of New Naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione and Anthra-9,10-quinone Dyes from Furan-2,3-diones

by
Şevket Hakan Üngören
Department of Chemistry, Faculty of Arts and Sciences, Bozok University, Yozgat, Turkey
Molecules 2009, 14(4), 1429-1437; https://doi.org/10.3390/molecules14041429
Submission received: 11 March 2009 / Revised: 26 March 2009 / Accepted: 30 March 2009 / Published: 2 April 2009
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Abstract

:
Novel naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione and anthra-9,10-quinone dyes were synthesized in good yield from furan-2,3-diones using 1,2-diaminoanthra-9,10-quinone and 1,4-diaminoanthra-9,10-quinone. The chromophores were characterized by molecular spectroscopy methods.

Graphical Abstract

1. Introduction

Anthra-9,10-quinones and their condensed derivatives with heterocycles such as indanthrone (Pigment Blue 60, I), anthrapyrimidine (Pigment Yellow 108, II) and Vat Yellow 3 (III) (Figure 1) possess brilliant hues and very good fastness and represent an important group of vat dyes for the textile industry [1,2]. In addition to these properties, some anthra-9,10-quinone dyes are widely used in other fields, such as in medicine and food chemistry [3] and high-technology systems [4]. Consequently, anthra-9,10-quinones are interesting compounds from the viewpoint of both their reactions and applications.
Furan-2,3-diones (1) have been shown to be very useful synthons for the preparation of various heterocycles. These compounds show typical carbonyl and lactone reactions, depending on the structures of the nucleophiles involved [5,6,7,8]. For example, furan-2,3-diones undergo cyclocondensations with 1,2-diamines to provide the corresponding quinoxalines and aromatic amines react with furan-2,3-diones to give the corresponding Schiff bases and pyrrole-2,3-dione derivatives, depending on the reaction times and temperature [5,9].
Molecules 14 01429 g001 550
Figure 1. Some commercial vat dyes.
Figure 1. Some commercial vat dyes.
Molecules 14 01429 g001
Furan-2,3-diones (1) can offer many possibilities for the construction of various heterocyclic dyes including the new naphtho[2,3-f]quinoxaline and anthra-9,10-quinone derivatives reported herein. In this work we present new anthra-9,10-quinone (2) and naphtho[2,3-f]quinoxaline (3) dyes derived from the reactions of some furan-2,3-diones with 1,2-diaminoanthra-9,10-quinone (1,2-DAAQ) and 1,4-diaminoanthra-9,10-quinone (1,4-DAAQ), acting as bifunctional nucleophiles.

2. Results and Discussion

Furan-2,3-dione starting materials 1a-f were prepared according to the literature [10,11,12,13]. The C5 atom of compounds 1a-d smoothly reacted with the amino group of 1,2-DAAQ and 1,4-DAAQ to give compoubds 2 under mild conditions and in high yields (75-90%, Scheme 1).
Molecules 14 01429 g003 550
Scheme 1. Synthesis of compounds 2.
Scheme 1. Synthesis of compounds 2.
Molecules 14 01429 g003
Reaction conditions: (i) Benzene, RT, 48 h.
Due to the greater reactivity of the amino group attached to the C2 atom of 1,2-DAAQ, compared with the amino group attached to the C1 atom of 1,2-DAAQ, 1,2-DAAQ was modified from the amino group attached to C2-position of 1,2-DAAQ to give 2e. On the other hand, the amino group attached to the C2 atom of 1,2-DAAQ did not react with the C5 atom of 1a at higher temperature, but reacted with the C3 atom of 1a by forming a Schiff base, which was not isolated (as outlined in Scheme 2). Through attack of the second amino group on the lactone carbonyl group, ring opening occurs. The reactions of 1,2-DAAQ with 1b,c,e,f run via the samereaction pathways to give 3 in nearly quantitative yields of 90-96% in boiling benzene. This proposed mechanism is similar to that reported in the literature for the reaction pathways of furan-2,3-diones with 1,2-diamino nucleophiles [9,14].
Molecules 14 01429 g004 550
Scheme 2. Synthesis of compounds 3.
Scheme 2. Synthesis of compounds 3.
Molecules 14 01429 g004
Reaction conditions: (ii) Benzene, reflux, 2 h.
The structures of 2 and 3 were confirmed by spectroscopic data and agree with those found for similar compounds [4,9,14,15]. In the NMR spectra, the methine proton signal (low intensity) also revealed that compound 2 occurs as tautomers (2A and 2B), with tautomer 2B as a minor contributor in DMSO-d6 solutions (Scheme 3). The 13C-NMR spectroscopic data of 2 also agree with the proposed tautomeric structures.
Molecules 14 01429 g005 550
Scheme 3. Tautomeric forms (2A and 2B) of 2a-e in DMSO-d6.
Scheme 3. Tautomeric forms (2A and 2B) of 2a-e in DMSO-d6.
Molecules 14 01429 g005
There was indication of tautomeric forms 3A (and 3B as a minor contributor) in 3a,f (but not 3b,c,e) in their 1H-NMR spectra in DMSO-d6 solution (Scheme 4). However, there was no signal for the methine proton belonging to the tautomer 3C in DMSO-d6 solution. The 13C-NMR spectra of 3 could not be recorded due to its very low solubility in organic solvents, but the condensation was verified by the detection of the [MH+] and [MH+-H2O] signals.
Molecules 14 01429 g006 550
Scheme 4. Tautomeric forms (3A-C) of 3a,f in DMSO-d6.
Scheme 4. Tautomeric forms (3A-C) of 3a,f in DMSO-d6.
Molecules 14 01429 g006
The UV-vis absorption spectra of 3a-c,e in DMF at a concentration of 3.333 x 10-5 mol/L are shown in Figure 2. The results are also listed in Table 1. In the visible region, the molar absorption coefficients and the absorption maxima of compounds 3 were observed in the range 1.119x104 to 1.545x104 dm3 mol-1 cm-1 (380-394 nm), 1.161x104 to 1.557x104 (397-412 nm), 1.467x104 to 1.842x104 (498-515 nm), there being no significant difference between them. The visible absorption spectrum is dominated by the characteristic anthraquinone bands in the region 380-400 nm [15].
Molecules 14 01429 g002 550
Figure 2. UV-Vis spectra of compound 3 in DMF.
Figure 2. UV-Vis spectra of compound 3 in DMF.
Molecules 14 01429 g002
Table
Table 1. UV-Vis spectral data of 3.
Table 1. UV-Vis spectral data of 3.
CompoundsUV-Vis
λ1-4max(nm),
ε1-4 (liter mol-1 cm-1)
3a274, 380,397,498,
2.592x1041.398x1041.416x1041.716x104
3b293,394,412,515,
3.066x1041.545x1041.557x1041.842x104
3c275,382,400,501,
2.652x1041.119x1041.161x1041.467x104
3e278,386,402,507,
2.865x1041.434x1041.518x1041.677x104

3. Experimental Section

3.1. General

Solvents were purchased from Merck and Carlo Erba. Diaminoanthra-9,10-quinones were purchased from Aldrich and used without further purification. 1H- and 13C-NMR spectra were recorded using a Bruker Ultrashield spectrometer operating at 300.13 MHz (1H) and 75.47 MHz (13C). UV-vis spectra: Shimadzu UV-1280 spectrophotometer. IR Spectra: Jasco Plus Model 460 FTIR spectrometer; in cm-1. Elemental analyses (C, H, N) were performed using a Leco CHNS-O 932. Melting points were measured with an Electrothermal 9200 apparatus. GC/MS measurements were performed using a gas chromatograph (Model 6890 Series)-mass selective detector (Model 5973N) system (Agilent Technologies).

3.2. General Procedure for the Preparation of Compounds 2a-e

Compound 1 (1 mmol) and 1,2-/1,4-DAAQ (1 mmol) in benzene (60 mL) was stirred for 48 h. The precipitate 2 was filtered off and recrystallized from DMF.
4-[(4-Amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-3-benzoyl-2-oxo-4-phenylbut-3-enoic acid (2a): Obtained from 1a (0.278 g, 1 mmol) and 1,4-DAAQ (0.238 g, 1 mmol). Mp. 195-196 °C as dark-blue crystals (0.415 g, 80%); 1H-NMR (DMSO-d6): δ = 13.50 (1H, s, NH), 8.77-6.35 (16H, m, aromatic), 7.16 (2H, s, NH2, br), 4.89 (Ar-CO-CH-CO, tautomer B), COOH not observed; 13C-NMR (DMSO-d6): δ = 193.29, 192.53, 188.81, 184.79, 183.47, 181.49 (C=O), 157.60, 152.96, 150.81, 147.19, 139.82, 137.98, 135.72, 135.04, 134.82, 134.55, 134.12, 134.05, 133.95, 133.84, 133.71, 133.47, 133.08, 132.68, 132.20, 132.07, 130.92, 130.47, 129.98, 129.70, 129.57, 129.40, 129.29, 129.12, 129.04, 128.86, 128.69, 128.15, 128.00, 127.87, 127.06, 126.46, 126.20, 124.43, 120.96, 118.32, 113.17, 111.94, 110.63, 110.20, 107.97, 93.69 (C=C, arom., aliph.), 64.05 (-CH-); IR (KBr) ν 3450 (OH, br); 3445, 3427 (NH2); 3302 (NH); 1724, 1690, 1670, 1636 cm-1 (C=O); Anal. Calcd for C31H20N2O6 (516.5): C, 72.09; H, 3.90; N, 5.42. Found: C, 72.26; H, 3.88; N, 5.28.
4-[(4-Amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-3-(4-methoxybenzoyl)-4-(4-methoxy-phenyl)-2-oxobut-3-enoic acid (2b): Obtained from 1b (0.338 g, 1 mmol) and 1,4-DAAQ (0.238 g, 1 mmol). Mp 215-216 °C as black crystals (0.503 g, 87%); 1H-NMR (DMSO-d6): δ = 13.55, 13.48 (1H, d, NH), 8.97-6.70 (14H, m, aromatic), 7.07 (2H, s, NH2, br), 4.72 (Ar-CO-CH-CO, tautomer B), 3.86, 3.79 (6H, s, OCH3), COOH not observed; 13C-NMR (DMSO-d6): δ = 192.73, 191.76, 191.50, 184.62, 183.51, 181.49 (C=O, C=N), 164.44, 163.45, 162.77, 161.41 (C=C-OCH3, tautomer A and B ), 157.78, 147.20, 135.07, 134.56, 134.12, 133.98, 133.08, 132.70, 131.79, 131.72, 131.36, 131.04, 129.91, 129.29, 128.72, 127.59, 127.08, 126.47, 126.21, 114.77, 114.56, 113.54, 107.97, 91.94 (C=C, arom., aliph.), 65.24 (-CH-) 36.24, 34.64, 31.23 (OCH3); IR (KBr) ν 3455 (OH, br); 3425 (NH2); 3300 (NH); 1726, 1686, 1664, 1638 cm-1 (C=O); Anal. Calcd for C33H24N2O8 (576.6): C, 68.75; H, 4.20; N, 4.86. Found: C, 68.84; H, 4.40; N, 4.81.
4-[(4-Amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-3-(4-methylbenzoyl)-4-(4-methylphenyl)-2-oxobut-3-enoic acid (2c): Obtained from 1c (0.306 g, 1 mmol) and 1,4-DAAQ (0.238 g, 1 mmol). Mp 220-221°C as navy-blue crystals (0.493 g, 90%); 1H-NMR (DMSO-d6): δ = 13.54, 13.49 (1H, d, NH), 8.77-6.62 (14H, m, aromatic), 7.58 (2H, s, NH2, br), 4.79 (Ar-CO-CH-CO, tautomer B), 3.45 (1H, s, COOH, br), 2.41, 2.31 (14H, s, CH3); 13C-NMR (DMSO-d6): δ = 192.95, 192.69, 192.61, 187.08, 183.55, 181.49 (C=O, C=N), 157.69, 150.24, 147.21, 145.48, 135.11, 134.56, 134.00, 133.90, 133.33, 133.15, 132.70, 130.99, 130.09, 129.87, 129.79, 129.46, 129.38, 129.30, 128.80, 128.17, 127.88, 127.18, 127.11, 126.49, 126.21, 118.36, 110.22, 107.95 (C=C, arom., alph.), 63.83 (-CH-), 21.71, 21.55 (CH3); IR (KBr) ν 3480 (OH, br); 3442 (NH2); 3308 (NH); 1725, 1689, 1671, 1663, 1638 cm-1 (C=O); Anal. Calcd for C33H24N2O6 (544.6): C, 72.78; H, 4.44; N, 5.14. Found: C, 72.92; H, 4.35; N, 4.96.
3-Acetyl-4-[(4-amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-4-(4-methylphenyl)-2-oxobut-3-enoic acid (2d): Obtained from 1d (0.230 g, 1 mmol) and 1,4-DAAQ (0.238 g, 1 mmol). Mp 174-175 °C as brown crystals (0.419 g, 90%); 1H-NMR (DMSO-d6): δ = 13.54, 13.44 (1H, d, NH), 8.92-6.86 (10H, m, aromatic), 7.58 (2H, s, NH2, br), 4.64 (Ar-CO-CH-CO, tautomer B), 3.51 (1H, s, COOH, br), 2.39 (3H, s, COCH3), 2.22 (3H, s, C=C-CH3); 13C-NMR (DMSO-d6): δ = 200.05, 192.45, 186.70, 183.39, 181.47 (C=O, C=N), 152.97, 150.05, 147.19, 146.02, 136.21, 135.72, 134.92, 134.54, 133.92, 133.76, 133.09, 132.69, 131.21, 130.20, 130.04, 129.88, 129.70, 129.37, 129.27, 128.07, 127.00, 126.41, 126.20, 117.89, 116.76, 109.96, 107.95, 105.96 (C=C, arom., alph.), 36.25 (COCH3), 21.59 (CH3); IR (KBr) ν 3475 (OH, br); 3432 (NH2); 3300 (NH); 1734, 1685, 1666, 1637, 1638 cm-1 (C=O); Anal. Calcd for C27H20N2O6 (468.4): C, 69.22; H, 4.30; N, 5.98. Found: C, 69.16; H, 4.15; N, 5.75.
4-[(1-Amino-9,10-dioxo-9,10-dihydroanthracen-2-yl)amino]-3-benzoyl-2-oxo-4-phenylbut-3-enoic acid (2e): Obtained from 1a (0.278 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol). Mp 255-256 °C as brown crystals (0.386 g, 75%); 1H-NMR (DMSO-d6): δ = 15.23 (1H, s, NH), 8.31-6.94 (16H, m, aromatic), 7.16 (2H, s, NH2, br), 3.38 (1H, s, br, COOH); 13C-NMR (DMSO-d6): δ = 194.27, 191.87, 188.77, 186.80, 185.32, 181.44 (C=O, C=N), 144.54, 142.51, 142.14, 134,56, 134.29, 133.54, 131,07, 129.63, 129.15, 128.43, 128.10, 127.86, 127.66, 127.51, 127.02, 126.60, 126.41, 125.63, 124.56, 124.18, 116.88, 109.01 (C=C, arom., alph.); IR (KBr) ν 3435 (OH, br, NH2); 3211 (NH); 1717, 1658, 1649, 1639 cm-1 (C=O); Anal. Calcd. for C31H20N2O6 (516.5): C, 72.09; H, 3.90; N, 5.42%. Found: C, 72.39; H, 3.72; N, 5.61.

3.3. General Procedure for the Preparation of Compounds 3a-c,e,f

Compound 1 (1 mmol) and 1,2-DAAQ (1 mmol) in benzene (40 ml) was refluxed for 2 h. The red-coloured precipitate (3) was filtered off and recrystallized from DMSO.
3-(1-Benzoyl-2-oxo-2-phenylethyl)naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione (3a): Obtained from 1a (0.278 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol). Mp 341-343 oC; 0.517 g, 94%; 1H-NMR (DMSO-d6): δ = 15.70, 15.07 (1H, s, OH, br), 13.25, 12.27 (1H, s, NH-C=O, br), 8.33-6.79 (16H, m, Ar-H); IR (KBr) ν 3435 (OH), 3210 (NH), 3072, 2925 (C-H), 1694, 1661, 1651, 1621 cm-1 (C=O); MS (ESI)+: m/z 498 (1%) [M+H]+; Anal. Calcd for C31H18N2O5 (498.5): C, 74.69; H, 3.64; N, 5.62. Found: C, 74.78; H, 3.68; N, 5.60.
3-[1-(4-Methoxybenzoyl)-2-(4-methoxyphenyl)-2-oxoethyl]naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione (3b): Obtained from 1b (0.338 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol); Mp 347-349 oC; 0.517 g, 92%; 1H-NMR (DMSO-d6): δ = 15.45 (1H, s, OH, br), 12.45 (1H, s, NHCO, br), 8.48-6.70 (14H, m, Ar-H), 3.80, 3.74 (6H, s, OCH3); IR (KBr) ν 3437 (OH), 3214 (NH), 3069, 2926 (C-H), 1695, 1664, 1654, 1638 cm-1 (C=O); MS (ESI)+: m/z 559 (5%) [M+H]+, m/z 541 (6%) [MH-H2O]+; Anal. Calcd for C33H22N2O7 (558.5): C, 70.96; H, 3.97; N, 5.02. Found: C, 70.79; H, 3.93; N, 5.17.
3-[1-(4-Methylbenzoyl)-2-(4-methylphenyl)-2-oxoethyl]naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione (3c): Obtained from 1c (0.306 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol); Mp 315-317 oC; 0.473 g, 90%; 1H-NMR (DMSO-d6): δ = 15.50 (1H, s, OH, br), 12.43 (1H, s, NHCO), 8.29-7.06 (14H, m, Ar-H), 2.34, 2.26 (6H, s, CH3); IR (KBr) v 3432 (OH), 3200 (NH), 3071, 2914 (C-H), 1693, 1663, 1656, 1638 cm-1 (C=O); MS (ESI)+: m/z 526 (13%) [M+H]+, m/z 525 (25%) [M]+; Anal. Calcd for C33H22N2O5 (526.5): C, 75.28; H, 4.21; N, 5.32. Found: C, 75.04; H, 4.29; N, 5.49.
3-[1-(3,4-Dimethoxybenzoyl)-2-(3,4-dimethoxyphenyl)-2-oxoethyl]naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione (3e): Obtained from 1e (0.398 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol); Mp 309-311 oC; 0.587 g, 95%; 1H-NMR (DMSO-d6): δ = 15.44 (1H, s, OH, br), 12.35 (1H, s, NHCO), 8.33-6.88 (12H, m, Ar-H), 3.81, 3.79, 3.75, 3.48 (12H, s, OCH3); IR (KBr) v 3436 (OH), 3253 (NH), 3075, 2932 (C-H), 1698, 1660, 1654, 1640 cm-1 (C=O); MS (ESI)+: m/z 619 (6%) [M+H]+, m/z 601 (2%) [MH-H2O]+; Anal. Calcd for C35H26N2O9 (618.6): C, 67.96; H, 4.24; N, 4.53. Found C, 68.17; H, 4.24; N, 4.60.
3-[(3E)-1-Benzoyl-2-oxo-4-phenylbut-3-en-1-yl]naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione (3f): Obtained from 1f (0.304 g, 1 mmol) and 1,2-DAAQ (0.238 g, 1 mmol); Mp 307-308 oC; 0.472 g, 90%; 1H-NMR (DMSO-d6): δ = 15.64, 14.55 (1H, s, OH, br), 12.35, 12.11 (1H, s, NH), 8.28-6.82 (16H, m, Ar-H), 7.74 (1H, d, J = 15.4 Hz, CH=), 6.64 (1H, d, J = 15.3 Hz, CH=); IR (KBr) v 3435 (OH), 3213 (NH), 3062, 2853 (C-H), 1696, 1664, 1657, 1638 cm-1 (C=O); MS (ESI)+: m/z 525 (6%) [M+H]+, m/z 508 (3%) [MH-H2O]+; Anal. Calcd for C33H20N2O5 (524.5): C, 75.56; H, 3.84; N, 5.34. Found: C, 75.53; H, 3.80; N, 5.41.

4. Conclusions

We have designed and easily synthesized novel naphtho[2,3-f]quinoxaline-2,7,12(1H)-triones and anthra-9,10-quinones in good to excellent yields as potential vat dyes from furan-2,3-diones. Their spectroscopic properties in solution and in the solid state are reported. For commercial dye production, reactions with high yields and relatively straightforward chemistry are preferred. It was seen that furan-2,3-diones have good reactivity to meet these expectations. We believe that preparation of various heterocyclic dyes based on furan-2,3-dione chemistry might make a contribution to the development of high performance pigments. Performances of new dyes will be tested in future studies.

Acknowledgements

The author is very grateful to Dr. İrfan Koca and Ress. Assist. Bilal Nişancı for technical assistance.

References and Notes

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  • Sample Availability: Samples of the compounds 2a-e and 3a,b,c,e,f are available from the authors.

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Üngören, Ş.H. Synthesis of New Naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione and Anthra-9,10-quinone Dyes from Furan-2,3-diones. Molecules 2009, 14, 1429-1437. https://doi.org/10.3390/molecules14041429

AMA Style

Üngören ŞH. Synthesis of New Naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione and Anthra-9,10-quinone Dyes from Furan-2,3-diones. Molecules. 2009; 14(4):1429-1437. https://doi.org/10.3390/molecules14041429

Chicago/Turabian Style

Üngören, Şevket Hakan. 2009. "Synthesis of New Naphtho[2,3-f]quinoxaline-2,7,12(1H)-trione and Anthra-9,10-quinone Dyes from Furan-2,3-diones" Molecules 14, no. 4: 1429-1437. https://doi.org/10.3390/molecules14041429

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