Supporting Information
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- Κλείτος Μήτζου
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1 Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General remarks. 1 H-NMR spectra were recorded on a 300 MHz spectrometer in CDCl 3 ELMER 983 spectrometer. Mass spectra were recorded with a HP-5989 instrument and HRMS was measured by a Finnigan MA+ mass spectrometer. Satisfactory CHN microanalyses were obtained with a Carlo-Erba 1106 analyzer. Melting points are uncorrected. All reactions were monitored by TLC with Huanghai GF 254 silica gel coated plates. Flash Column Chromatography was carried out using mesh silica gel. General procedure. Under ambient atmosphere, arylaldehyde 2 (0.10 mmol), aromatic amine 3 (0.10 mmol), anhydrous MgSO 4 (0.15 mmol) and acetonitrile (1.0 ml) were added into a Schlenk reaction tube. After the reaction mixture was stirred for 2.0 hrs at room temperature, MCP 1 (0.1 mmol) and Mont. KSF (50 mg) were added successively. The reaction mixture was stirred at room temperature (20 o C) for another appropriate hours. The solvent was removed under reduced pressure and the residue was purified by a flash column chromatography (SiO 2 ) (eluent: petroleum ether/etoac = 20/1) to give the corresponding aza-diels-alder reaction product 4. using tetramethylsilane as an internal standard. Infrared spectra were measured on a PERKIN- 7-Trifluoromethyl-4,4-bis(4-methoxyphenyl)-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 - cyclopropyl)quinoline 4a. A white solid, Mp: o C, 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.76 (s, 3H, OCH 3 ), 3.86 (s, 3H, OCH 3 ), 4.30 (s, 1H, NH), 5.11 (s, 1H), 6.70 (d, 2H, J = 9.0 Hz, Ar), (m, 6H, Ar), 7.08 (d, 1H, J = 8.4 Hz, Ar), (m, 5H, Ar), 7.54 (d, 2H, J = 8.4 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.22, 25.44, 29.66, 53.39, 55.08, 55.54, 58.02, , , , (q, J C-F = 270 Hz), (q, J C-F = 29.7 Hz), , , , , , (q, J C-F = 4.8 Hz), , , , , , , , IR (CH 2 Cl 2 ) ν 3378, 3002, 2929, 2837, 1713, 1606, 1507, 1
2 1251, 831, 752, 705 cm -1. MS (%) m/e 515 (M +, 3.73), 406 (100). HRMS calcd. for C 32 H 28 F 3 NO 2 : , Found: Anal. Calcd. for C 32 H 28 F 3 NO 2 : C, 74.55%; H, 5.47%; N, 2.72%. Found: C, 74.48%; H, 5.63%; N, 2.58%. The X-ray data of 4a has been deposited in CCDC with number Empirical Formula: C 32 H 28 F 3 NO 2 ; Formula Weight: ; Crystal Color, Habit: colorless, prismatic; Crystal Dimensions: 0.20 x 0.20 x 0.30 mm; Crystal System: orthorhombic; Lattice Type: primitive; Lattice Parameters: a= (2) Å, b= (18) Å, c= (3) Å, α= 90 o, β= 90 o, γ= 90 o, V= (12) Å 3 ; Space group: Pbca; Z value= 8; D calc = g/cm 3 ; F 000 = 2160; µ(mokα)= 1.98 cm -1 ; Diffractometer: Rigaku AFC7R; Residuals: R; Rw: , ,4-Bis(4-methoxyphenyl)-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4b. A white solid, Mp: o C, 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.76 (s, 3H, OCH 3 ), 3.84 (s, 3H, OCH 3 ), (m, 1H, NH), 5.09 (s, 1H), (q, 4H, J = 6.9 Hz, Ar), (m, 5H, Ar), 7.10 (t, 1H, J = 6.9 Hz, Ar), (m, 5H, Ar), 7.60 (d, 2H, J = 8.7 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.39, 26.03, 29.66, 53.41, 55.17, 55.55, 58.00, , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3690, 3054, 2987, 1605, 1421, 1265, 895, 739, 705 cm -1. MS (%) m/e 447 (M +, 2.68), 338 (21.35), 43 (100). HRMS Calcd. for C 31 H 29 NO 2 : , Found:
3 4-(4-Ethoxyphenyl)-4-methyl-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)- quinoline 4c. A white solid, Mp: o C, (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 2H), (m, 2H), (m, 6H, CH 3 ), (m, 3H, CH 2 +NH), 4.60 (s, 1H), (m, 4H, Ar), (m, 9H, Ar). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 2H), (m, 2H), 1.41 (t, 3H, J = 7.2 Hz, CH 3 ), 1.95 (s, 3H, CH 3 ), (m, 3H, CH 2 +NH), 5.03 (s, 1H), (m, 4H, Ar), (m, 9H, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 3.80, 6.32, 14.94, 23.50, 28.69, 43.66, 57.62, 63.20, , , , , , , , , , , , , , (trans-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.86, 6.21, 14.97, 27.08, 30.64, 45.96, 58.50, 63.27, , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3054, 2987, 1422, 1265, 896, 740 cm -1. MS (%) m/e 369 (M +, 21.08), 246 (100). HRMS Calcd. for C 26 H 27 NO: , Found: Trifluoromethyl-4-(4-ethoxyphenyl)-4-methyl-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 - cyclopropyl)quinoline 4d. A white solid, Mp: o C, (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.43 (t, 3H, J = 7.5 Hz, CH 3 ), 1.49 (s, 3H, CH 3 ), 4.00 (q, 2H, J = 7.5 Hz), 4.31 (s, 1H), 5.05 (s, 1H), (m, 4H, Ar), (m, 2H, Ar), (m, 6H, Ar). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.42 (t, 3H, J = 7.5 Hz, CH 3 ), 1.93 (s, 3H, CH 3 ), (m, 3H, CH 2 +NH), 5.33 (s, 1H), (m, 4H, Ar), (m, 2H, Ar), (m, 6H, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 5.84, 7.53, 11.78, 26.40, 30.53, 43.76, 57.63, 60.01, , , , , , (q, J C-F = 243 Hz), , , , , (q, J C-F = 27.6 Hz), , , (q, J C-F = 7.5 Hz), , , , , (transisomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 3.58, 6.25, 14.83, 27.96, 29.69, 45.99, 58.29, 63.22, , , , , , (q, J C-F = 245 Hz), , , , , (q, J C-F = 28.2 Hz), , , (q, J C-F = 8.4 Hz), , , , , IR (CH 2 Cl 2 ) ν 3054, 2987, 1422, 1265, 896, 740, 705 cm -1. MS (%) m/e 437 (M +, 95.77), 422 (27.51), 394 (54.38), 314 (100). HRMS Calcd. for C 27 H 26 F 3 NO: , Found:
4 7-Trifluoromethyl-4,4-bis(4-methylphenyl)-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4e. A white solid, Mp: o C. 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 2.25 (s, 3H, CH 3 ), 2.38 (s, 3H, CH 3 ), 4.22 (s, 1H, NH), 5.10 (s, 1H), (m, 6H, Ar), 7.12 (d, 1H, J = 8.4 Hz, Ar), (m, 7H, Ar), 7.55 (d, 2H, J = 8.1 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.25, 7.32, 20.77, 20.87, 25.20, 56.17, 57.97, , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3026, 1615, 1582, 1484, 1265, 739 cm -1. MS (%) m/e 483 (M +, 16.01), 390 (100). HRMS Calcd. for C 32 H 28 F 3 N: , Found: Methoxy-4-(4-ethoxyphenyl)-4-methyl-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4f. A white solid, Mp: o C, (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 2H), (m, 2H), 1.40 (t, 3H, J = 6.9 Hz, CH 3 ), 1.41 (s, 3H, CH 3 ), 3.90 (s, 3H, OCH 3 ), (m, 3H, CH 2 +NH), 5.03 (s, 1H), (m, 5H, Ar), (m, 2H, Ar), (m, 5H, Ar). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.40 (t, 3H, J = 6.6 Hz, CH 3 ), 2.00 (s, 3H, CH 3 ), 3.91 (s, 3H, OCH 3 ), (m, 3H, CH 2 +NH), 4.65 (s, 1H), (m, 5H, Ar), (m, 2H, Ar), (m, 5H, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75MHz, TMS) δ 1.86, 6.18, 6.28, 23.63, 28.63, 43.68, 55.32, 56.94, 63.12, , , , , , , , , , , , , , , (anti-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 0.99, 3.72, 14.87, 27.16, 30.48, 46.00, 55.37, 58.18, 63.18, , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3044, 2978, 1416, 1265, 739, 705 cm -1. MS (%) m/e 399 (M +, 29.93), 276 (72.08), 136 (100). HRMS Calcd. for C 27 H 29 NO 2 : , Found: ,4-Bis(4-methoxyphenyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4g. A white solid, Mp: o C. 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.76 (s, 3H, OCH 3 ), 3.81 (s, 3H, OCH 3 ), 3.84 (s, 3H, OCH 3 ), 4.08 (s, 1H, NH), 5.05 (s, 1H), (m, 4H, Ar), (m, 2H, Ar), (m, 5H, Ar), 7.09 (t, 1H, J = 8.7 Hz, Ar), (m, 2H, Ar), 7.59 (d, 2H, J = 8.4 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.30, 26.08, 54.99, 55.09, 55.48, 57.35, , , , , , , , , , , , , , , , , , IR 4
5 (CH 2 Cl 2 ) ν 3054, 1606, 1265, 896, 742 cm -1. MS (%) m/e 477 (M +, 9.26), 368 (100). HRMS Calcd. for C 32 H 31 NO 3 : , Found: ,4-Bis(4-methoxyphenyl)-2-(4-ethoxyphenyl)-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl) quinoline 4h. A white solid, Mp: o C, 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.35 (t, 3H, J = 6.9 Hz), 3.76 (s, 3H, OCH 3 ), 3.86 (s, 3H, OCH 3 ), (m, 5H, OCH 3 +CH 2 ), 5.06 (s, 1H), (m, 5H, Ar), (m, 4H, Ar), (m, 5H, Ar), 7.68 (d, 2H, J = 9.0 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.77, 14.94, 26.57, 30.92, 53.45, 55.19, 55.95, 58.22, 64.16, , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3054, 2987, 1607, 1422, 1265, OCH 3 ): , Found: , 705 cm -1. MS (%) m/e 491 (M +, 21.90), 382 (53.19). HRMS Calcd. for C 33 H 33 NO 3 (M- 6-Ethoxy-4-(4-ethoxyphenyl)-4-methyl-2-phenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4i. A white solid, Mp: o C. (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 2H), (m, 1H), (m, 1H), (m, 9H, CH 3 ), (m, 5H, 2CH 2 +NH), 4.57 (s, 1H), (m, 4H, Ar), (m, 8H, Ar). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 3H), (m, 1H), (m, 6H, 2CH 3 ), 1.94 (s, 3H, CH 3 ), (m, 5H, 2CH 2 +NH), 4.96 (s, 1H), (m, 4H, Ar), (m, 8H, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 3.90, 6.34, 14.84, 15.04, 27.39, 28.92, 43.91, 57.49, 63.13, , , , , , , , , , , , (trans-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.82, 6.14, 14.87, 23.62, 27.42, 29.65, 45.65, 58.73, 63.18, 64.04, , , , , , , , , , , IR (CH 2 Cl 2 ) ν 2979, 1506, 1248, 1049, 738 cm -1. MS (%) m/e 413 (M +, 46.13), 290 (100). HRMS Calcd. for C 28 H 31 NO 2 : , Found: (4-Methoxyphenyl)-4-phenyl-2-chlorophenyl-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4j. A white solid, Mp: o C. (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 1H), (m, 3H), 3.76 (s, 3H, CH 3 O), 4.06 (s, 1H, NH), 5.06 (s, 1H), (m, 4H, Ar), (m, 12H, Ar), (m, 1H, Ar). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.85 (s, 3H, CH 3 O), 4.06 (s, 1H, NH), 5.08 (s, 1H),
6 6.73 (m, 4H, Ar), (m, 12H, Ar), (m, 1H, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.53, 14.17, 22.65, 29.65, 38.71, 57.51, , , , , , , , , , , , , , , , , (trans-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.30, 11.41, 19.15, 25.65, 30.27, 55.19, , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3059, 2978, 1420, 1265, 899, 739 cm -1. MS (%) m/e 451 (M +, 54.07), 372 (97.11), 342 (100). HRMS Calcd. for C 30 H 26 NO: ; Found: ,4-Bis(4-methoxyphenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)- quinoline 4k. A white solid, Mp: o C, 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.75 (s, 3H, OCH 3 ), 3.84 (s, 3H, OCH 3 ), 4.04 (s, 1H, NH), 5.05 (s, 1H), (m, 4H, Ar), (m, 4H, Ar), 7.10 (t, 1H, J = 8.7 Hz, Ar), (m, 5H, Ar), 7.56 (d, 2H, J = 8.7 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.33, 22.59, 26.01, 29.58, 55.11, 55.41, 57.47, , , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3054, 2987, 1422, 1265, 896, 739 cm -1. MS (%) m/e 481 (M +, 11.54), 372 (100). HRMS (Maldi) Calcd. for C 31 H 28 ClNO 2 : , Found: ,4-Bis(4-methoxyphenyl)-2-(4-nitrophenyl)-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)- quinoline 4l. A yellow solid, Mp: o C, 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 3.74 (s, 3H, OCH 3 ), 3.84 (s, 3H, OCH 3 ), 4.09 (s, 1H, NH), 5.16 (s, 1H), (m, 4H, Ar), (m, 5H, Ar), 7.13 (t, 1H, J = 6.9 Hz, Ar), 7.53 (t, 4H, J = 9.0 Hz, Ar), 8.17 (d, 2H, J = 9.0 Hz, Ar). 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.45, 7.51, 26.27, 55.04, 55.16, 55.36, 57.93, , , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3055, 2988, 1712, 1422, 1363, 1266, 1223, 896, 739, 705 cm -1. MS (%) m/e 492 (M +, 16.56), 462 (35.88), 383 (100), 367 (31.81), 338 (27.32). Anal. Calcd. for C 31 H 28 N 2 O 4 : C, 75.59%; H, 5.73%; N, 5.69 %. Found: C, %; H, 5.74 %; N, 5.43%. 6
7 4-(4-Ethoxyphenyl)-4-methyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydrospiro(3,1 -cyclopropyl)quinoline 4m. A white solid, Mp: o C, (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 2H), (m, 2H), (m, 6H, CH 3 ), 3.90 (s, 3H, CH 3 ), (m, 3H, CH 2 +NH), 4.54 (s, 1H), (m, 1H, Ar), (m, 4H), (m, 4H), (m, 3H). (trans-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.46 (t, 3H, J = 6.6 Hz), 1.93 (s, 3H, CH 3 ), 3.91 (s, 3H, OCH 3 ), (m, 3H, CH 2 +NH), 4.98 (s, 1H), (m, 1H, Ar), (m, 4H), (m, 4H), (m, 3H). (cisisomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 3.65, 6.21, 14.86, 23.44, 28.73, 43.54, 55.15, 56.92, 63.14, , , , , , , , , , , , , (trans-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 1.74, 6.04, 14.89, 27.09, 30.56, 45.86, 55.19, 57.77, 63.21, , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3054, 2987, 1606, 1510, 1422, 1265, 896, 742, 705 cm -1. MS (%) m/e 399 (M +, 18.21), 276 (100). HRMS Calcd. for C 27 H 29 NO 2 : , Found: Ethoxy-4-(4-methoxyphenyl)-4-phenyl-2-nitrophenyl-1,2,3,4-tetrahydrospiro(3,1 - cyclopropyl)quinoline 4n. An orange solid, Mp: o C. (cis-isomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), (t, 3H, J = 4.5 Hz), 3.74 (s, 3H, CH 3 O), (m, 3H, CH 2 +NH), 5.11 (s, 1H), (m, 2H, Ar), (m, 12H, Ar), 8.15 (d, 2H, J = 8.7 Hz, Ar). (transisomer) 1 H NMR (CDCl 3, 300 MHz, TMS) δ (m, 4H), 1.33 (t, 3H, J = 7.2 Hz), 3.85 (s, 3H, CH 3 O), (m, 3H, CH 2 +NH), 5.13 (s, 1H), (m, 2H, Ar), (m, 12H, Ar), 8.15 (d, 2H, J = 8.7 Hz, Ar). (cis-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 7.68, 11.87, 14.86, 26.05, 34.00, 40.21, 55.14, 57.87, , , , , , , , , , , , , , , , , , (trans-isomer) 13 C NMR (CDCl 3, 75 MHz, TMS) δ 3.38, 11.38, 14.83, 22.85, 33.42, 38.86, 55.00, 56.32, , , , , , , , , , , , , , , , , , IR (CH 2 Cl 2 ) ν 3067, 2978, 1416, 1265, 896, 740 cm -1. MS (%) m/e 506 (M +, 88.73), 397 (100). HRMS Calcd. for C 32 H 30 N 2 O 4 : , Found:
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