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Wet cyanuric chloride promoted efficient synthesis of amidoalkyl naphthols under solvent-free conditions
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Chinese Chemical Letters 20 (2009) 383–386 www.elsevier.com/locate/cclet
Wet cyanuric chloride promoted efficient synthesis of amidoalkyl naphthols under solvent-free conditions Gholam Hossein Mahdavinia a,*, Mohammad A. Bigdeli b a
Department of Chemistry, Islamic Azad University-Marvdasht Branch, Marvdasht, Iran b Faculty of Chemistry, Tarbiat Moalem University, 49 Mofateh St., Tehran, Iran Received 29 August 2008
Abstract An efficient and direct procedure has been developed for the preparation of amidoalkyl naphthols by a one-pot condensation of aryl aldehydes, 2-naphthol and urea or amides, in the presence of wet-cyanuric chloride (wet-TCT) as a catalyst. The reactions were carried out under solvent-free media. The present methodology offers several advantages such as excellent yields, simple procedure and eco-friendly reaction condition. # 2008 Gholam Hossein Mahdavinia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: One-pot; Cyanuric chloride; Catalyst; Amidoalkyl naphthol; Multicomponent
Multicomponent reactions (MCRs) have attracted considerable attention since they are performed without need to isolate any intermediate during their processes; this reduces time and saves both energy and raw materials [1–4]. They have merits over two-component reactions in several aspects including the simplicity of a one-pot procedure, possible structural variations and building up complex molecules. Bigenilli [5–7], Ugi [8–10], Passerini [11,12] and Mannich [13–15] reactions are some examples of MCRs. Nevertheless, development and discovery of new MCRs is still in much demands. In this context, ortho-quinone methides (O-QMs) have been used in many tandem processes [16–18], but only limited work has appeared with their reaction with nucleophiles [19–21]. Recently we have reported [22] the reaction of 2-naphthol and aldehydes in the presence of wet-TCT to form xanthenes. The reaction proceeds through the in situ formation of ortho-quinone methides and 2-naphthol acted as a nucleophile (Scheme 1). We have now extended this wet-TCT catalyzed procedure using urea or amides (as nucleophiles) along with 2naphthol and aldehydes to produce the corresponding amidoalkyl naphthols (Scheme 2). Recently, some procedures for the syntheses of amidoalkyl naphthols are reported using p-TsOH [23], I2 [24], montmorillonite K10 [25], K5CoW12O403H2O [26] and sulfamic acid [27]. These protocols, however, suffer from the use of expensive or highly acidic catalysts and require prolonged reaction times. Furthermore, the yields of the corresponding amidoalkyl naphthols are not always satisfactory. Due to the importance of these
* Corresponding author. E-mail address: [email protected] (G.H. Mahdavinia). 1001-8417/$ – see front matter # 2008 Gholam Hossein Mahdavinia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. doi:10.1016/j.cclet.2008.12.018
384
G.H. Mahdavinia, M.A. Bigdeli / Chinese Chemical Letters 20 (2009) 383–386
Scheme 1.
Scheme 2.
compounds, the introduction of a milder, faster and more eco-friendly methods accompanied with higher yields is desirable. As part of our ongoing research concerning the use of economically and easily available materials as catalysts for various organic transformations [28–32] in this communication, we wish to report a simple and efficient application of TCT as a catalyst in the synthesis of amidoalkyl naphthols, under mild conditions. The condensation of mixture of benzaldehyde 1a (1 mmol) with 2-naphthol 2 (1 mmol) and acetamide 3a (1.1 mmol) in the presence of wet-TCT (0.1 mmol) was carried out at 100 8C for 10 min under solvent-free conditions (Scheme 2). The reaction proceeded smoothly and gave the corresponding amidoalkyl naphthol 4a as the sole product in 91% yield. Water was added to the reaction mixture and simply filtering the mixture and the filtrate gave the crude product, which was purified by crystallization in ethanol to obtain 4a as white solid. In the course of optimization of the reaction conditions, an increase in the reaction time was not proved to be useful. TCT (10 mol%) was the optimum amount of catalyst and larger amounts of the catalyst (20 mol%) did not improve the yields while decreasing the amount of catalyst decreased the yields. The reaction worked well with electron-withdrawing (NO2, CN, Cl, Br, F) as well as electron-donating (Me, MeO, OH) groups, giving various amidoalkyl naphthol derivatives in 90–96% yields. As shown in Table 1, the method is general and includes a variety of functional groups. In summary, a novel and highly efficient methodology for the synthesis of amidoalkyl naphthols by condensation reaction of aldehydes, 2-naphtol and acetamide or benzamide or urea in the presence of catalytic amounts of wet-TCT under solvent-free conditions is reported. This protocol describes a very fast, user friendly, ‘green’ and low-cost procedure for the synthesis of these products. Furthermore, TCT is a catalyst with cyanuric acid as by product that is removable by washing with water. This easy removal of the catalyst makes this method a better choice for chemical industries. 1. Experimental The products (4a–s) were isolated and characterized by physical and spectral data. 1H NMR spectra were recorded on Bruker Avance-300 MHz spectrometers with 7–10 mmol/L solutions in CDCl3 in the presence of tetramethylsilane as internal standard. IR spectra were recorded using a PerkinElmer 843 spectrometer with KBr plates. Elemental analyses were measured on a PerkinElmer 2400 series II analyzer. Melting points were determined on Electro thermal 9100, and are not corrected. Synthesis of amidoalkyl naphthols: general procedure A mixture of aldehyde (1 mmol), 2-naphthol (1 mmol), acetamide or benzamide or urea (1.1 mmol), TCT (0.1 mmol) and H2O (2 drops) were mixed and stirred for 2 min at room temperature and then temperature was raised
G.H. Mahdavinia, M.A. Bigdeli / Chinese Chemical Letters 20 (2009) 383–386
385
Table 1 TCT-mediated synthesis of amidoalkyl naphthols. Entry
Ar
R
Product
Time (min)
Yield (%) a
m.p. (8C) Found
Reported 242-244[25] 228–229[26] 228–230[25] 203–205[27] — 212–215[25] 203–205[27] 194–196[27] 234–236[27] 192–193[27] 177–178[27] 193–194[27] — 216–217[27] 230–232[27] 172–174[27] 168–169[27] 170–172[27] — 255–259[26] 184–186[27]
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
C6H5 4-ClC6H5 4-BrC6H5 4-FC6H5 4-CNC6H5 3-NO2C6H5 3-MeOC6H5 2-ClC6H5 C6H5 4-MeC6H5 4-ClC6H5 4-FC6H5 4-CNC6H5 3-NO2C6H5 C6H5
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Ph Ph Ph Ph Ph Ph NH2
4a 4b 4c 4d 4e 4f 4g 4h 4i 4j 4k 4l 4m 4n 4o
10 10 10 10 12 8 14 8 10 12 10 10 12 8 14
91 90 92 92 90 96 90 94 90 90 92 93 92 95 90
243–245 229–231 230–232 207–209 261–262 213–214 202–204 196–197 230–232 204–205 176–177 195–196 176–178 215–216 231–232
16 17 18 19
4-ClC6H5 4-BrC6H5 4-CNC6H5 3-NO2C6H5
NH2 NH2 NH2 NH2
4p 4q 4r 4s
12 12 14 8
90 92 92 94
168–170 174–176 330–332 254–256
a
Crude yields.
to 100 8C and maintained for the appropriate time (Table 1). After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (5 mL) and stirred for 5 min in 80 8C. The resulting solid products were collected by filtration and were recrystallized from ethanol. Selected spectral (IR, 1H NMR,
13
C NMR) and analytical data
Compound 4e: IR (KBr): 3380, 3053, 2232, 1629, 1529, 1513, 1476, 1440, 1336, 1283, 1248, 1067, 883, 859, 825 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 1.99 (s, 3H), 7.13 (d, 1H, J = 7.94 Hz), 7.18–7.40 (m, 5H), 7.69–7.82 (m, 5H), 8.50 (d, 1H, J = 7.94 Hz), 10.05 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 22.48, 47.81, 108.73, 117.87, 118.33, 118.92, 122.52, 122.88, 126.61, 126.89, 128.38, 128.61, 129.74, 131.93, 132.15, 148.88, 153.25, 169.58; Anal. Calcd. for C20H16N2O2: C, 75.95; H, 5.06, N, 8.86. Found: C, 75.90; H, 5.11, N, 8.78. Compound 4m: IR (KBr): 3241, 3063, 2229, 1644, 1591, 1519, 1459, 1433, 1402, 1247, 1240, 1084, 962, 839, 815 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 7.22 (d, 1H, 8.42 Hz), 7.28–7.97 (m, 15H), 8.67 (d, 1H, J = 8.42 Hz), 10.33 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 36.42, 116.33, 117.68, 118.43, 118.95, 123.16, 123.98, 124.71, 127.16, 127.32, 127.35, 128.40, 128.67, 128.77, 129.51, 130.61, 130.71, 132.45, 148.01, 151.52, 168.52; Anal. Calcd. for C25H18N2O2: C, 79.36; H, 4.76, N, 7.41. Found: C, 79.22; H, 4.87, N, 7.83. Compound 4r: IR (KBr): 3306, 3067, 2231, 1664, 1593, 1520, 1505, 1461, 1435, 1403, 1250, 1242, 1146, 965, 842, 817 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 6.85 (s, 1H), 7.44–7.65 (m, 5H), 7.79–7.97 (m, 5H), 8.66 (d, 1H, J = 8.43 Hz), 10.15 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 36.42, 108.82, 116.32, 117.67, 123.15, 124.71, 124.73, 127.16, 128.68, 128.76, 129.51, 130.61, 130.71, 132.45, 148.00, 150.98, 159.98; Anal. Calcd. for C19H15N3O2: C, 71.92; H, 4.73, N, 13.25. Found: C, 72.11; H, 4.67, N, 13.34. References [1] I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45 (2004) 8625. [2] S.H. Mashraqui, M.B. Patil, H.D. Mistry, S. Ghadigaonkar, A. Meetsma, Chem. Lett. 33 (2004) 1058. [3] A. Chetia, C.J. Saikia, K.C. Lekhok, R.C. Boruah, Tetrahedron Lett. 45 (2004) 2649.
386 [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15] [16] [17] [18] [19] [20] [21] [22] [23] [24] [25] [26] [27] [28] [29] [30] [31] [32]
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Chinese Chemical Letters 20 (2009) 383–386 www.elsevier.com/locate/cclet
Wet cyanuric chloride promoted efficient synthesis of amidoalkyl naphthols under solvent-free conditions Gholam Hossein Mahdavinia a,*, Mohammad A. Bigdeli b a
Department of Chemistry, Islamic Azad University-Marvdasht Branch, Marvdasht, Iran b Faculty of Chemistry, Tarbiat Moalem University, 49 Mofateh St., Tehran, Iran Received 29 August 2008
Abstract An efficient and direct procedure has been developed for the preparation of amidoalkyl naphthols by a one-pot condensation of aryl aldehydes, 2-naphthol and urea or amides, in the presence of wet-cyanuric chloride (wet-TCT) as a catalyst. The reactions were carried out under solvent-free media. The present methodology offers several advantages such as excellent yields, simple procedure and eco-friendly reaction condition. # 2008 Gholam Hossein Mahdavinia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: One-pot; Cyanuric chloride; Catalyst; Amidoalkyl naphthol; Multicomponent
Multicomponent reactions (MCRs) have attracted considerable attention since they are performed without need to isolate any intermediate during their processes; this reduces time and saves both energy and raw materials [1–4]. They have merits over two-component reactions in several aspects including the simplicity of a one-pot procedure, possible structural variations and building up complex molecules. Bigenilli [5–7], Ugi [8–10], Passerini [11,12] and Mannich [13–15] reactions are some examples of MCRs. Nevertheless, development and discovery of new MCRs is still in much demands. In this context, ortho-quinone methides (O-QMs) have been used in many tandem processes [16–18], but only limited work has appeared with their reaction with nucleophiles [19–21]. Recently we have reported [22] the reaction of 2-naphthol and aldehydes in the presence of wet-TCT to form xanthenes. The reaction proceeds through the in situ formation of ortho-quinone methides and 2-naphthol acted as a nucleophile (Scheme 1). We have now extended this wet-TCT catalyzed procedure using urea or amides (as nucleophiles) along with 2naphthol and aldehydes to produce the corresponding amidoalkyl naphthols (Scheme 2). Recently, some procedures for the syntheses of amidoalkyl naphthols are reported using p-TsOH [23], I2 [24], montmorillonite K10 [25], K5CoW12O403H2O [26] and sulfamic acid [27]. These protocols, however, suffer from the use of expensive or highly acidic catalysts and require prolonged reaction times. Furthermore, the yields of the corresponding amidoalkyl naphthols are not always satisfactory. Due to the importance of these
* Corresponding author. E-mail address: [email protected] (G.H. Mahdavinia). 1001-8417/$ – see front matter # 2008 Gholam Hossein Mahdavinia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. doi:10.1016/j.cclet.2008.12.018
384
G.H. Mahdavinia, M.A. Bigdeli / Chinese Chemical Letters 20 (2009) 383–386
Scheme 1.
Scheme 2.
compounds, the introduction of a milder, faster and more eco-friendly methods accompanied with higher yields is desirable. As part of our ongoing research concerning the use of economically and easily available materials as catalysts for various organic transformations [28–32] in this communication, we wish to report a simple and efficient application of TCT as a catalyst in the synthesis of amidoalkyl naphthols, under mild conditions. The condensation of mixture of benzaldehyde 1a (1 mmol) with 2-naphthol 2 (1 mmol) and acetamide 3a (1.1 mmol) in the presence of wet-TCT (0.1 mmol) was carried out at 100 8C for 10 min under solvent-free conditions (Scheme 2). The reaction proceeded smoothly and gave the corresponding amidoalkyl naphthol 4a as the sole product in 91% yield. Water was added to the reaction mixture and simply filtering the mixture and the filtrate gave the crude product, which was purified by crystallization in ethanol to obtain 4a as white solid. In the course of optimization of the reaction conditions, an increase in the reaction time was not proved to be useful. TCT (10 mol%) was the optimum amount of catalyst and larger amounts of the catalyst (20 mol%) did not improve the yields while decreasing the amount of catalyst decreased the yields. The reaction worked well with electron-withdrawing (NO2, CN, Cl, Br, F) as well as electron-donating (Me, MeO, OH) groups, giving various amidoalkyl naphthol derivatives in 90–96% yields. As shown in Table 1, the method is general and includes a variety of functional groups. In summary, a novel and highly efficient methodology for the synthesis of amidoalkyl naphthols by condensation reaction of aldehydes, 2-naphtol and acetamide or benzamide or urea in the presence of catalytic amounts of wet-TCT under solvent-free conditions is reported. This protocol describes a very fast, user friendly, ‘green’ and low-cost procedure for the synthesis of these products. Furthermore, TCT is a catalyst with cyanuric acid as by product that is removable by washing with water. This easy removal of the catalyst makes this method a better choice for chemical industries. 1. Experimental The products (4a–s) were isolated and characterized by physical and spectral data. 1H NMR spectra were recorded on Bruker Avance-300 MHz spectrometers with 7–10 mmol/L solutions in CDCl3 in the presence of tetramethylsilane as internal standard. IR spectra were recorded using a PerkinElmer 843 spectrometer with KBr plates. Elemental analyses were measured on a PerkinElmer 2400 series II analyzer. Melting points were determined on Electro thermal 9100, and are not corrected. Synthesis of amidoalkyl naphthols: general procedure A mixture of aldehyde (1 mmol), 2-naphthol (1 mmol), acetamide or benzamide or urea (1.1 mmol), TCT (0.1 mmol) and H2O (2 drops) were mixed and stirred for 2 min at room temperature and then temperature was raised
G.H. Mahdavinia, M.A. Bigdeli / Chinese Chemical Letters 20 (2009) 383–386
385
Table 1 TCT-mediated synthesis of amidoalkyl naphthols. Entry
Ar
R
Product
Time (min)
Yield (%) a
m.p. (8C) Found
Reported 242-244[25] 228–229[26] 228–230[25] 203–205[27] — 212–215[25] 203–205[27] 194–196[27] 234–236[27] 192–193[27] 177–178[27] 193–194[27] — 216–217[27] 230–232[27] 172–174[27] 168–169[27] 170–172[27] — 255–259[26] 184–186[27]
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
C6H5 4-ClC6H5 4-BrC6H5 4-FC6H5 4-CNC6H5 3-NO2C6H5 3-MeOC6H5 2-ClC6H5 C6H5 4-MeC6H5 4-ClC6H5 4-FC6H5 4-CNC6H5 3-NO2C6H5 C6H5
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Ph Ph Ph Ph Ph Ph NH2
4a 4b 4c 4d 4e 4f 4g 4h 4i 4j 4k 4l 4m 4n 4o
10 10 10 10 12 8 14 8 10 12 10 10 12 8 14
91 90 92 92 90 96 90 94 90 90 92 93 92 95 90
243–245 229–231 230–232 207–209 261–262 213–214 202–204 196–197 230–232 204–205 176–177 195–196 176–178 215–216 231–232
16 17 18 19
4-ClC6H5 4-BrC6H5 4-CNC6H5 3-NO2C6H5
NH2 NH2 NH2 NH2
4p 4q 4r 4s
12 12 14 8
90 92 92 94
168–170 174–176 330–332 254–256
a
Crude yields.
to 100 8C and maintained for the appropriate time (Table 1). After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (5 mL) and stirred for 5 min in 80 8C. The resulting solid products were collected by filtration and were recrystallized from ethanol. Selected spectral (IR, 1H NMR,
13
C NMR) and analytical data
Compound 4e: IR (KBr): 3380, 3053, 2232, 1629, 1529, 1513, 1476, 1440, 1336, 1283, 1248, 1067, 883, 859, 825 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 1.99 (s, 3H), 7.13 (d, 1H, J = 7.94 Hz), 7.18–7.40 (m, 5H), 7.69–7.82 (m, 5H), 8.50 (d, 1H, J = 7.94 Hz), 10.05 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 22.48, 47.81, 108.73, 117.87, 118.33, 118.92, 122.52, 122.88, 126.61, 126.89, 128.38, 128.61, 129.74, 131.93, 132.15, 148.88, 153.25, 169.58; Anal. Calcd. for C20H16N2O2: C, 75.95; H, 5.06, N, 8.86. Found: C, 75.90; H, 5.11, N, 8.78. Compound 4m: IR (KBr): 3241, 3063, 2229, 1644, 1591, 1519, 1459, 1433, 1402, 1247, 1240, 1084, 962, 839, 815 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 7.22 (d, 1H, 8.42 Hz), 7.28–7.97 (m, 15H), 8.67 (d, 1H, J = 8.42 Hz), 10.33 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 36.42, 116.33, 117.68, 118.43, 118.95, 123.16, 123.98, 124.71, 127.16, 127.32, 127.35, 128.40, 128.67, 128.77, 129.51, 130.61, 130.71, 132.45, 148.01, 151.52, 168.52; Anal. Calcd. for C25H18N2O2: C, 79.36; H, 4.76, N, 7.41. Found: C, 79.22; H, 4.87, N, 7.83. Compound 4r: IR (KBr): 3306, 3067, 2231, 1664, 1593, 1520, 1505, 1461, 1435, 1403, 1250, 1242, 1146, 965, 842, 817 cm 1; 1H NMR (300 MHz, CDCl3, d ppm): 6.85 (s, 1H), 7.44–7.65 (m, 5H), 7.79–7.97 (m, 5H), 8.66 (d, 1H, J = 8.43 Hz), 10.15 (sbr, 1H); 13C NMR (75 MHz, CDCl3, d ppm): 36.42, 108.82, 116.32, 117.67, 123.15, 124.71, 124.73, 127.16, 128.68, 128.76, 129.51, 130.61, 130.71, 132.45, 148.00, 150.98, 159.98; Anal. Calcd. for C19H15N3O2: C, 71.92; H, 4.73, N, 13.25. Found: C, 72.11; H, 4.67, N, 13.34. References [1] I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45 (2004) 8625. [2] S.H. Mashraqui, M.B. Patil, H.D. Mistry, S. Ghadigaonkar, A. Meetsma, Chem. Lett. 33 (2004) 1058. [3] A. Chetia, C.J. Saikia, K.C. Lekhok, R.C. Boruah, Tetrahedron Lett. 45 (2004) 2649.
386 [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15] [16] [17] [18] [19] [20] [21] [22] [23] [24] [25] [26] [27] [28] [29] [30] [31] [32]
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