Ionic liquid effect over the Biginelli reaction under homogeneous and heterogeneous catalysis
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1 Supporting Information for Ionic liquid effect over the Biginelli reaction under homogeneous and heterogeneous catalysis Haline G. O. Alvim, a,b Tatiani B. de Lima, c Heibbe C. B. de Oliveira, a Fabio C. Gozzo, c Julio L. de Macedo, d Patricia V. Abdelnur, e Wender A. Silva, b * and Brenno A. D. Neto, a * a Laboratory of Medicinal and Technological Chemistry, University of Brasilia (IQ-UnB). Campus Universitario Darcy Ribeiro, CEP , P.O.Box 4478, Brasilia-DF, Brazil. b Laboratory for Bioactive Compounds Synthesis, University of Brasilia (IQ-UnB). Campus Universitario Darcy Ribeiro, CEP , P.O.Box 4478, Brasilia-DF, Brazil. c Institute of Chemistry, University of Campinas, Campinas, SP, Brazil. d Laboratory of Catalysis, Institute of Chemistry, University of Brasília, P.O. Box 4478, CEP , Brasília - DF, Brasil. e Embrapa Agroenergia, PqEB s/n Av. W3 Norte (final), Edifício Embrapa Agroenergia, CEP: , P.O.Box wender@unb.br, brenno.ipi@gmail.com S1
2 Summary Scheme S1 Page S3 Figure S1 Page S4 Figure S2 Page S4 Spectroscopic data for all compounds Pages S4-S6 Cartesian coordinates, energy and thermal corrections for all calculated structures Pages S7-S13 References Page S13 S2
3 Scheme S1. The three accepted mechanism for the Biginelli reaction. S3
4 Yield (%) Time (min) Figure S1. Reaction profile (model reaction) conducted at 90 ºC, BMI.BF 4 (1 ml) and 3.00 mmol of each reagent and 7 mol% of the catalyst (MSI.Fe 2 Cl 7 ) affording 4a. All yields refer to the isolated product N + N H N + N. N + N SO 3 H O S O O + H m/z Figure S2. ESI(+)-QTOF product ion spectrum of the catalyst (MSI) 3 PW. MSI.Cl: 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.10 (s, 1H), 7.77 (s, 1H), 7.71 (s, 1H), 4.30 (t, 2H, J = 7.0 Hz), 3.87 (s, 3H), 2.45 (t, 2H, J = 7.1 Hz), (m, 2H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 136.9, 123.8, 122.4, 47.7, 47.5, 35.7, Ethyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4a): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.22 (s, 1H), 7.76 (s, 1H), (m,5h), 5.14 (s,1h), 3.97 (q, 2H, J = 6.8 Hz), 2.24 (s, 3H), 1.07 (t, 3H, J = 6.8 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 165.7, 152.6, 148.8, 145.3, 128.8, 127.7, 126.7, 99.7, 59.6, 54.4, 18.2, FT- IR (KBr, cm -1 ): 3252, 3109, 2972, 1728, 1689, 1645, 1468, 1230, 1097, 778. m.p C (literature C) and Rf 0.60 (Hexane/ AcOEt 7:3). White solid, method a 87%, method b 99%, method c 99%, method d 85% e method e 99%. S4
5 5-Acetyl-4-phenil-6-methyl-3,4-dihydropyrimidin-2(1H)-one (4b): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.19 (s, 1H), 7.84 (s, 1H), (m, 5H), 5.25 (s, 1H), 3.43 (q, J = 6.2 Hz), 1.06 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 194.7, 152.6, 148.6, 144.6, 128.9, 128.8, 110.0, 56.5, 30.7, FT-IR (KBr, cm -1 ): 3287, 3241, 2914, 1706, 1603, 1466, 1248, 764. m.p C (literature C) and Rf 0.64 (Hexane/AcOEt 7:3). White solid, method a 76%, method b 96%, method c 82%, method d 79% e method e 99%. Ethyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4c): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), (s, 1H), (m, 5H), 5.94 (d, 1H, J = 3.0 Hz), 4.75 (q,2h, J = 6.7Hz), 3.05 (s, 3H), 1.84 (t, 3H, J = 7.1 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 174.7, 166.9, 165.4, 145.9,130.1, 129.0, 128.8, 100.7, 60.1, 53.9, 17.7, FT-IR (KBr, cm - 1 ): 3322, 3466, 3176, 3111, 1670, 1575, 1470, 1277, 1197, 1105, 696. m.p C (literature C) and Rf 0.50 (Hexane/ AcoEt 7:3). Yellow solid, method a 43%, method b 88%, method c 99%, method d 98% e method e 99%. Ethyl-4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4d): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.93 (s, 1H), 8.46(s, 1H), 7.65 (t, 1H, J = 7.9 Hz), (m, 3H), 5.82 (d,1h, J = 2.7 Hz), 4.76 (q, 2H, J = 7.2 Hz), 2.99 (s, 3H), 1.87 (t, 3H, J = 7.1 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 165.9, 157.8, 152.7, 148.6, 146.7, 129.8, 128.8, 117.3, 114.6, 99.8, 59.6, 54.3, 18.2, FT-IR (KBr, cm -1 ): 3514, 3364, 3250, 3104, 2978, 1722, 1638, 1600, 1475, 1305, 1221, 1056, 771. m.p C (literature C) and Rf 0.33 (Hexane/ AcOEt 7:3). White solid, method a 99%, method b 37%, method c 66%, method d 60% e method e 75%. Ethyl 6-methyl-4-(3-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4e): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.59 (s, 1H), 9.44 (s, 1H), 7.09 (t, 1H, J = 7.9 Hz), 6.65 (m, 3H), 5.09 (d,1h, J = 2.7 Hz), 3.98 (q, 2H, J = 6.7 Hz), 2.27 (s, 3H), 1.08 (t, 3H, J = 6.9 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 174.6, 165.6, 157.9, 145.6, 145.2, 129.9, 117.5, 115.0, 113.8, 101.2, 60.5, 54.4, 17.6, FT-IR (KBr, cm -1 ): 3304, 3179, 3109, 2982, 1662, 1573, 1479, 1375, 1293, 1196, 1117, 747. m.p C (literature C) and Rf 0.24 (Hexane/ AcOEt 7:3). Yellow solid, method a 50%, method b 98%, method c 33%, method d 98% e method e 50%. Ethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4f): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.39 (s, 1H), (m, 4H), 3.89 (q, 2H, J = 2.7 Hz), 2.28 (s, 3H), 1.10 (t,3h, J = 6.9 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 165.1, 151.8, 149.5, 147.7, 147.0, 133.0, 130.3, 122.4, 121.0, 98.3, 59.4, 53.6, 17.9, FT-IR (KBr, cm -1 ): 3330, 3213, 3105, 2965, 1709, 1631, 1520, 1456, 1343, 1221, 1084, 810, 686, 530. m.p C (literature C) and Rf 0.85 (Hexane/ AcOEt 7:3). White solid, method a 41%, method b 81%, method c 69%, method d 63% e method e 98%. 5-acetyl-3,4-dihydro-6-methyl-4-(3-nitrophenyl)-pyrimidin- 2(1H)-one (4g): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.37 (s, 1H), (m. 4H), 5.4 (d, 1H, J = 3Hz), 2.33 (s, 3H), 2.19 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 194.1, 152.0, 149.2, 147.9, 146.5, 133.0, 130.2, 122.4, 121.1, 109.5, 53.0, 30.7, FT-IR (KBr, cm -1 ): 3357, 3271, 3057, 1721, 1683, 1591, 1532, 1347, 1239, 764, 693, 578. m.p C (literature C) and Rf 0.88 (Hexane/ AcOEt 7:3). Yellow solid method a 57%, method b 93%, method c 54%, method d 63% e method e 98%. 1,2,3,4-tetrahydro-6-methyl-2-oxo-5-pyrimidinecarboxylic acid ethyl ester (4h): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 4.58 (q, 2H, J = 3.7 Hz), 3.43 (d, 2H), 1.07 (t, 3H, J = 7.0 Hz). FT-IR (KBr,cm -1 ): 3356, 2928, 1621, 1571, 1242, 664. m.p C (literature C). White solid, method a 56%, method b 82%, method c 86%, method d 76% e method e 94%. 1,2,3,4-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-5-pyrimidinecarboxylic acid ethyl ester (4i): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.15 (s, 1H), 8.91 (s, 1H), 7.67 (s, 1H), (m, 3H), 5.09 (s, 1H), 4.44 (q,2h), 3.99 (s, 3H), 2.46 (s, 3H), 1.06 (t, 3H, J = 5.2 Hz). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 165.9, 152.9, 148.2,147.7, , 136.3, 118.0, 115.7, 111.2, 100.1, 59.6, 55.9, 54.0, 18.1, FT-IR (KBr, cm -1 ): , 3115, 2972, 2922, 1703, 1642, 1509, 1219, 1086, 782. m.p C (literature C) and Rf 0.85 (Hexane/ AcOEt 7:3). White solid, method a 59%, method b 43%, method c 46%, method d 80% e method e 99%. S5
6 2,3,4,6,7,8-hexahydro-4-(3-hydroxyphenyl)-2-thioxo-quinazolin-5(1H)-one (4j): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.64 (s, 1H), 9.42 (s, 1H), (m, 4H), 5.08 (d, J = 3.3 Hz), 3.38 (s, 1H), 2.47 (q, 1H, J = 4.2 Hz), 1.96 (s, 1H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 194.4, 184.2, 174.8, 157.8, 151.0, 145.1, 129.9, 117.4, 113.7, 109.5, 52.1, 36.8, 25.7, FT- IR (KBr, cm -1 ): 3408, 3284, 2916, 1620, 1447, 1356, 1175, 760. m.p C (literature C) and Rf 0.81 (MeOH 100%). Yellow solid, method a 76%, method b 59%, method c 59%, method d 59% e method e 60%. 2,3,4,6,7,8-hexahydro-4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-5(1H)-quinazolinone (4k): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H, NH), 9.57, 9.23, (m, 4H), 5.07 (d, 1H, J = 3.3 Hz), 1.99 (s, 2H), 1.74, 1.19 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 196.7, 194.3, 184.2, 174.8, 157.8, 151.0, 145.1, 129.9, 117.4, 109.5, 52.1, 36.8, 32.4, 25.7, FT-IR (KBr, cm -1 ): 3400, 2957, 1644, 1585, 1463, 1364, 1193, 793, 692, 472. m.p. 220 C (literature C) and Rf 0.17 (hexano/ AcoEt 7:3). Yellow solid, method a 21%, method b 87%, method c 21%, method d 53% e method e 60%. 5-acetyl-3,4-dihydro-6-methyl-4-(2-nitrophenyl)-pyrimidin-2(1H)-one (4l): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.08 (s, 1H), (m. 4H), 4.13 (d, 1H, J = 3.9 Hz), 2.31 (s,3h), 2.11 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 157.8, 154.9, 148.5, 136.8, 134.6, 133.1, 129.0, 128.9, 124.6, 56.6, 29.0, FT-IR (KBr, cm -1 ): 3470, 3442, 3371, 3286, 1672, 1592, 1514, 1372, 1199, 787, 586. m.p. 200 C (literature C) and Rf 0.64 (Hexane/ AcOEt 7:3). Yellow solid, method a 65%, method b 98%, method c 70%, method d 70% e method e 86%. 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester (4m): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): 9.67 (s, 1H), 9.12 (s, 1H), (m, 2H), (m, 2H), 5.44 (d, 1H, J = 2.7 Hz), 4.13, (q, 2H, J = 1.8 Hz), 1.77 (d, 3H), 1.21 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 176.8, , 150.9, 130.1, 129.2, 124.1, 121.3, 116.8, 100.0, 81.8, 61.2, 48.6, 23.8, FT-IR (KBr, cm -1 ): 3328, 3201, 2975, 1721, 1565, 1505, 1383, 1260, 1182, 1089, 908, 758, 523. m.p C (literature C) and Rf 0.35 (Hexane/ AcOEt 7:3). Yellow solid, method a 12%, method b 36%, method c 15%, method d 97% e method e 60%. 4-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid- ethyl ester (4n): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.63 (s, 1H), 6.88 (s, 1H), 6.72 (d, 2H, J = 1.5 Hz), 6.00 (s, 2H), 5.09 (d, 1H, J = 3.6 Hz), 2.29 (s, 3H), 1.12 (t, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 174.4, 166.5, 147.8, 147.1, 145.5, 137.8, 134.1, 120.1, 108.6, 107.2, 101.5, 60.0, 54.1, 17.6, FT-IR (KBr, cm -1 ): 3320, 3185, 2978, 2892, 1163, 1573, 1492, 1336, 1235, 1202, 1107, 742. m.p. 175 C (literature C) and Rf 0.55 (Hexane/ AcOEt 7:3). Yellow solid, method a 35%, method b 85%, method c 19%, method d 71% e method e 74%. 5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-pyrimidin-2(1H)-one (4o): 1 H NMR (DMSO-d6, 300 MHz, δ ppm): (s, 1H), 9.94 (s, 1H), 8.56 (s, 1H), 7.88 (t, 1H, J = 7.1 Hz), 7.42 (t, 1H, J =10.5 Hz), 5.94 (s, 1H), 3.04 (s, 3H), 2.85 (s, 3H). 13 C NMR (DMSO-d6, 75 MHz, δ ppm): 194.9, 157.9, 152.6, 148.4, 146.1, 130.0, 117.5, 114.8, 113.7, 110.0, 54.3, 30.7, FT-IR (KBr, cm -1 ): 3248, 3107, 2942, 1707, 1657, 1606, 1462, 1235, 742. m.p C (literature C) and Rf 0.77 (Hexane/ AcOEt 7:3). White solid, method a 76%, method b 99%, method c 33%, method d 65% e method e 85%. S6
7 Cartesian coordinates, energy and thermal corrections for all the calculated structures NTf 2 (trans) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree NTf 2 (cis) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S7
8 Int I E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree Int II E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S8
9 Int I + NTf 2 (cis) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree Counterpoise: BSSE energy = hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S9
10 Int I + NTf 2 (trans) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree Counterpoise: BSSE energy = hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S10
11 Int II + NTf 2 (cis) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree Counterpoise: BSSE energy = hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S11
12 Int II + NTf 2 (trans) E(M06-2X/ g(2d,2p)//B3LYP/6-31+G(d,p))= hartree Counterpoise: BSSE energy = hartree hartree hartree hartree Thermal correction to Gibbs Free Energy at K = hartree S12
13 References 1 Ramos,L. M.; Tobio, A. Y. P. L.; Santos, M. R.; Oliveira, H. C. B.; Gomes, A. F.; Gozzo, F. C.; Oliveira, A. L.; Neto, B. A. D. J. Org. Chem. 2012, 77, M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., GAUSSIAN 09, Revision A.02, Gaussian, Inc., Wallingford CT, P.J. Stephens, J.F. Devlin, C.F. Chabalowski, M.J. Frisch, J. Chem. Phys. 1993, 98, Sarli, V.; Huemmer, S.; Sunder-Plassmann, N.; Mayer, T. U.; Giannis, A. ChemBioChem 2005, 6, Shirini, F.; Zolfigol, M. A; Mollarazi, E. Synth.Commun.2006, 36, Kamal, A.; KrishnaJ = i, T.; Azhar, M. A.Catal. Commun. 2007, 8, Zheng, R.; Wang, X.; Xu, H.; Du, J. Synth. Commun. 2006, 36, Ghosh, R; Maiti, S.; Chakraborty, A. J. Mol. Catal. A: Chem. 2004, 217, 47. S13
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Supplementary Materials Figure S1. Chemical structures of phloracetophenone intermediates (2a, 2c 2g). 2a 2c 2d 2e 2f 2g Figure S2. Chemical structures of geranylacetophenone analogues (3a, 3c, 3e g).
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