multicomponent synthesis of 5-amino-4-
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1 Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean C. Kazmierczak 2, Roberta Cargnelutti 2, Diego Alves 1, Raquel G. Jacob 1 and Ricardo F. Schumacher* 1,2 Address: 1 LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box , Pelotas, RS, Brazil and 2 Departamento de Química, Universidade Federal de Santa Maria UFSM, , Santa Maria, RS, Brazil Ricardo F. Schumacher - ricardo.schumacher@ufsm.br *Corresponding author Experimental part S1
2 Contents General Information... S2 General procedure for the synthesis of 5-amino-4-(arylselanyl)pyrazoles (4)... S2 General procedure for the synthesis of diazo pyrazole derivative (6).. S3 Table S1. Crystallographic data and refinement parameters for 6 S8 Selected spectra S9 General Information: Reactions were monitored by TLC carried out on Merck silica gel (60 F254) by using UV light as visualizing agent and 5% vanillin in 10% H 2 SO 4 and heat as developing agents. Column chromatography was performed by using silica gel. Proton nuclear magnetic resonance spectra ( 1 H NMR) were obtained at 400 MHz with Bruker DPX 400 spectrometer. Spectra were recorded in CDCl 3 solutions. Chemical shifts are reported in ppm, referenced to tetramethylsilane (TMS) as the external reference. Hydrogen coupling patterns are described as singlet (s), doublet (d), triplet (t), double doublet (dd) and multiplet (m). Coupling constants (J) are reported in Hertz. Carbon-13 nuclear magnetic resonance spectra ( 13 C NMR) were obtained at 100 MHz with Bruker DPX 400 spectrometer. Chemical shifts are reported in ppm, referenced to the solvent peak of CDCl 3 (77.0 ppm). Low resolution mass spectra (MS) were obtained with Shimadzu GCMS-QP2010 mass spectrometer High resolution mass spectra (HRMS) were recorded on a Bruker Micro TOF-QII spectrometer. Melting point (m.p.) values were measured with a Marte PFD III instrument. Infrared spectra were measured using a Shimadzu Prestige- 21 IR spectrometer. A Cole Parmer-ultrasonic processor Model CPX 130, with a maximum power of 130 W, operating at amplitude of 60% and a frequency of 20 khz was used. General procedure for the synthesis of 5-amino-4-(arylselanyl)pyrazoles (4) To a 10 ml vial equipped with a reflux condenser containing a mixture of benzoylacetonitrile 1 (0.5 mmol), arylhydrazine 2 (0.7 mmol) and diaryl diselenide 3 (0.5 mmol) in MeCN (3 ml), molecular iodine (50 mol %) was added. Then the mixture was stirred at reflux temperature for a period of 48 hours. Under these conditions the expected product 4 was obtained and the progress of the reaction was monitored by TLC. The reaction mixture was poured in water (15 ml), extracted with ethyl acetate (3 10 ml), dried over MgSO 4 and concentrated under vacuum. The residue was purified by column S2
3 chromatography by using silica gel and a mixture of hexane/ethyl acetate (95:05) as eluent. General procedure for the synthesis of diazo pyrazole derivative (6) 1 5-Amino-4-(phenylselanyl)-1H-pyrazol 4a (0.5 mmol) was added to a 10 ml vial containing a mixture of 1,10-phenantroline (0.15 mmol), tert-butyl peroxide (1.5 mmol) and CuI (0.05 mmol) in dichloromethane (2 ml). Then, the mixture was stirred at room temperature for 2 hours and the expected product 5 was obtained. The progress of the reaction was monitored by TLC. The reaction mixture was received in water (10 ml), extracted with ethyl acetate (3 5 ml), dried over MgSO 4 and concentrated under vacuum. The residue was purified by column chromatography using silica gel and a mixture of hexane/ethyl acetate (90:10) as eluent. 1,3-Diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine (4a): Orange oil; Yield: 96%; IR (KBr, cm -1 ): 3450 (s), 3412 (s), 3055 (m), 2922 (w), 1946 (w), 1801 (w), 1600 (s), 1500 (s), 1475 (m), 1371 (m), 1111 (w), 970 (m), 759 (s), 690 (s). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), (m, 2H), (m, 6H), (m, 3H) 4.30 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ=153.6, 149.5, 138.6, 133.0, 132.9, 129.5, 129.2, 128.1, 128.1, , 127.6, 125.8, 123.6, 82.4 ppm. 77 Se NMR (CDCl 3, 76 MHz): δ= ppm. MS m/z (rel. int.): 391 (43), 389 (23), 311 (100), 293 (3), 208 (15), 155 (8). HRMS calcd. for C 21 H 18 N 3 Se: [M + H] Found: Phenyl-4-(phenylselanyl)-3-(p-tolyl)-1H-pyrazol-5-amine (4b): Reddish oil; Yield: 73%; IR (KBr, cm -1 ): 3433 (s), 3057 (w), 2916 (w), 1598 (s), 1502 (s), 1473 (m), 1367 (w), 1182 (w), 1020 (m), 970 (m), 732 (s), 665 (w). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 6H), 4.30 (s, 2H), 2.33 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ=153.7, 149.5, 137.9, 133.2, 130.6, 130.2, 129.6, 129.3, 128.9, , 127.6, 125.9, 123.7, 82.6, 21.2 ppm. 77 Se NMR (CDCl 3, 76 MHz): δ= ppm. MS m/z (rel. int.): 405 (37), 325 (100), 307 (2), 232 (3), 208 (13), 162 (4), 132 (15), 119 (14), 77 (35). HRMS calcd. for C 22 H 20 N 3 Se: [M + H] Found: S3
4 3-(4-methoxyphenyl)-1-phenyl-4-(phenylselanyl)-1Hpyrazol-5-amine (4c): Brownish oil; Yield: 35%; 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 4.28 (s, 2H), 3.75 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ= 159.6, 153.3, 149.4, 138.7, 133.1, 129.5, 129.2, 129.0, 127.8, 127.4, 125.8, 125.6, 123.5, 113.5, 82.1, 55.1 ppm. MS m/z (rel. int.): 421 (1), 408 (1), 345 (4), 280 (61), 265 (51), 146 (47), 131 (23), 119 (47), 104 (49), 77 (100). 3-(4-Bromophenyl)-1-phenyl-4-(phenylselanyl)-1H-pyrazol-5- amine (4d): Brown solid; m.p.: C; Yield: 78%; IR (KBr, cm -1 ): 3412 (m), 3055 (w), 2920 (w), 2850 (w), 1598 (s), 1575 (m), 1498 (s), 1436 (m), 1363 (m), 1008 (m), 912 (w), 829 (s), 665 (w). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), (m, 4H), (m, 1H), (m, 5H), 4.14 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ=152.3, 149.7, 138.6, 132.8, 132.0, 131.2, 129.6, 129.3, 127.9, 127.8, 126.0, 123.6, 123.4, 82.5 ppm. 77 Se NMR (CDCl 3, 76 MHz): δ= ppm. MS m/z (rel. int.): [M+2] 471 (40) [M+] 469 (51), 389 (99), 309 (7), 267 (5), 233 (4), 208 (33), 155 (13), 127 (15), 119 (28), 77 (100). HRMS calcd. for C 21 H 17 BrN 3 Se: [M + H] Found: (4-Chlorophenyl)-1-phenyl-4-(phenylselanyl)-1H-pyrazol-5- amine (4e): Brown oil; Yield: 81%; IR (KBr, cm -1 ): 3550 (m), 3414 (s), 3057 (m), 2920 (w), 1948 (w), 1884 (w), 1598 (s), 1531 (m), 1500 (s), 1454 (m), 1373 (m), 1087 (s), 759 (s), 659 (w). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), 7.41 (t, J=7.4 Hz, 2H), (m, 1H), (m, 2H), (m, 5H), 4.18 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ=152.4, 149.6, 138.6, 134.1, 132.8, 131.6, 129.6, 129.3, 129.1, 128.3, 128.0, 127.8, 126.1, 123.7, 82.5 ppm. MS m/z (rel. int.): [M+2] 427 (10) 425 (31), 421 (6), 347 (35), 345 (100), 309 (4), 267 (3), 233 (2), 208 (16), 180 (2), 162 (9), 153 (3), 177 (35). HRMS calcd. for C 21 H 17 ClN 3 Se: [M + H] Found: Phenyl-4-(phenylselanyl)-1-(m-tolyl)-1H-pyrazol-5-amine (4g): Brown oil; Yield: 63%; IR (KBr, cm -1 ): 3473 (m), 3408 (s), S4
5 3331 (m), 3097 (w), 2922 (w), 2852 (w), 1606 (s), 1575 (m), 1541 (s), 1496 (m), 1346 (s), 1109 (w), 966 (m), 742 (s), 657 (w). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 12H), 4.28 (s, 2H), 2.39 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ=153.4, 149.4, 139.8, 138.4, 133.1, 132.9, 129.2, 128.4, 128.1, 127.8, 127.7, 125.8, 124.8, 120.4, 82.1, 21.3 ppm. MS m/z (rel. int.): 405 (31), 391 (3), 325 (100), 283 (17), 248 (3), 222 (15), 146 (17). HRMS calcd. for C 22 H 20 N 3 Se: [M + H] Found: (2,5-Dimethylphenyl)-3-phenyl-4-(phenylselanyl)-1H-pyrazol-5- amine (4h): Orange oil; Yield: 52%; IR (KBr, cm -1 ): 3550 (s), 3415 (s), 3055 (w), 2920 (w), 2854 (w), 1616 (s), 1508 (w), 1367 (w), 1143 (w), 968 (m), 815 (m), 771 (m), 734 (m), 694 (m). 1 H NMR (CDCl 3, 400 MHz): δ=7.84 (d, J=8.1 Hz, 2H), (m, 6H), (m, 5H), 3.90 (s, 2H), 2.28 (s, 3H), 2.09 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ=153.1, 150.3, 139.7, 136.2, 134.2, 133.5, 133.3, 132.0, 129.2, 128.0, 127.9, 127.8, 127.7, 127.6, 127.5, 125.7, 80.3, 21.1, 17.4 ppm. MS m/z (rel. int.): 419 (85), 417 (45), 339 (100), 323 (16), 297 (5), 2,62 (12), 235 (38), 184 (6), 159 (15). HRMS calcd. for C 23 H 22 N 3 Se: [M + H] Found: (2,4-Dichlorophenyl)-3-phenyl-4-(phenylselanyl)-1Hpyrazol-5-amine (4i): Brown oil; Yield: 80%; IR (KBr, cm -1 ): 3550 (m), 3390 (s), 3248 (m), 3082 (s), 2915 (w), 2848 (w), 2362 (w), 1618 (s), 1537 (s), 1504 (s), 1469 (s), 1431 (m), 1296 (m), 1099 (m), 775 (s), 657 (m). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), (m, 9H), 4.02 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ=154.5, 150.9, 136.2, 134.6, 133.0, 132.9, 132.8, 130.8, 130.4, 129.3, 128.4, 128.3, 128.1, 127.9, 127.8, 125.9, 82.0 ppm. MS m/z (rel. int.): [M+2] 461 (37), [M+] 459 (55), 424 (100), 381 (50), 321 (8), 276 (17), 218 (11), 199 (14), 128 (41), 77 (60). HRMS calcd. for C 21 H 16 Cl 2 N 3 Se: [M + H] Found: (2,4-Difluorophenyl)-3-phenyl-4-(phenylselanyl)-1Hpyrazol-5-amine (4j): Brown solid; m.p.: C; Yield: 76%; IR (KBr, cm -1 ): 3550 (m), 3473 (s), 3412 (s), 3230 (w), 3051 (w), 2920 (w), 1637 (m), 1616 (s), 1597 (s), 1531 (m), 1363 (w), 831 (s), 723 (m), 620 (w). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 1H), (m, 3H), (m, 4H), (m, 1H), (m, 2H), 4.22 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ=162.5 (dd, J=241.2 e 11.1 Hz), (dd, J=241.2 e 11.1 Hz), 154.7, 151.0, 147.9, 143.4, 132.9, 132.7, 130.0, 129.9, 129.3, 128.3, 128.1, 127.8, S5
6 127.7, 127.1, 125.9, (dd, J= 12.1, 4.0 Hz), (dd, J= 22.5, 3.7 Hz), (dd, J=26.5, 23.6 Hz), 82.3 ppm. 77 Se NMR (CDCl 3, 76 MHz): δ= ppm. MS m/z (rel. int.): 427 (48), 425 (25), 383 (2), 347 (100), 305 (2), 244 (23), 218 (6), 155 (19), 128 (18). HRMS calcd. for C 21 H 16 F 2 N 3 Se: [M + H] Found: ,3-Diphenyl-4-(p-tolylselanyl)-1H-pyrazol-5-amine (4l): Orange oil; Yield: 54%; IR (KBr, cm -1 ): 3550 (m), 3477 (m), 3390 (s), 3250 (s), 3109 (s), 1881 (w), 1811 (w), 1743 (w), 1618 (s), 1575 (m), 1469 (s), 1431 (s), 1294 (m), 1139 (m), 1099 (s), 974 (s), 657 (m). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), 7.47 (t, J=7.5 Hz, 2H), (m, 4H), 7.15 (d, J=8.0 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 4.28 (s, 2H), 2.25 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ=153.5, 149.4, 138.6, 135.6, 132.9, 130.0, 129.5, 129.1, 128.1, 128.0, 127.9, 127.8, 127.5, 123.5, 82.7, 20.9 ppm. MS m/z (rel. int.): 405 (10), 328 (100), 312 (12), 298 (22), 142 (16), 77 (61). HRMS cald. for C 22 H 20 N 3 Se: [M + H] Found ((4-Methoxyphenyl)selanyl)-1,3-diphenyl-1H-pyrazol-5-amine (4m): Brown solid; m.p.: C; Yield: 63%; IR (KBr, cm -1 ): 3552 (w), 3442 (m), 3342 (m), 3053 (w), 2920 (w), 1884 (w), 1734 (w), 1602 (s), 1529 (m), 1600 (s), 1471 (s), 1452 (m), 1384 (m), 1170 (w), 1008 (s), 688 (s). 1 H NMR (CDCl 3, 400 MHz): δ= (m, 2H), (m, 2H), 7.29 (t, J=7.3 Hz, 2H), (m, 4H), 7.06 (d, J=7.0 Hz, 2H), 6.60 (d, J=6.9 Hz, 2 H), 4.16 (s, 2H), 3.53 ppm (s, 3H). 13 C NMR (CDCl 3, 100 MHz): δ= 158.4, 153.1, 149.3, 138.7, 133.1, 132.8, 130.0, 129.3, 127.9, 127.8, 127.3, 123.4, 122.8, 115.0, 83.7, 55.1 ppm. MS m/z (rel. int.): 421 (6), 347 (34), 345 (100), 327 (7), 309 (8), 281 (28), 267 (8), 253 (16), 235 (7), 207 (84), 191 (12), 155 (5), 119 (25), 104, (16), 77 (82). HRMS calcd. for C 22 H 20 N 3 OSe: [M + H] Found: ((4-Chlorophenyl)selanyl)-1,3-diphenyl-1H-pyrazol-5-amine (4n): Reddish solid; m.p.: C; Yield: 80%; IR (KBr, cm -1 ): 3435 (s), 3059 (m), 2924 (w), 2850 (w), 2733 (w), 2194 (w), 1948 (w), 1884 (w), 1600 (s), 1531 (m), 1500 (s), 1454 (m), 1373 (m), 1174 (w), 1087 (s), 759 (s), 659 (w). 1 H NMR (CDCl 3, 400 MHz): δ= 7.82 (d, J=7.9 Hz, 2H), 7.56 (d, J=7.5 Hz, 2H), 7.39 (t, J=7.7 Hz, 2H), (m, 4H), (m, 4H), (m, 1H), 4.22 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz) δ= 153.5, 149.5, 138.6, 132.9, 131.9, 131.4, 129.6, 129.3, 129.2, 128.2, 128.1, 127.8, 123.6, 113.8, 82.2 ppm. 77 Se NMR (CDCl 3, 76 MHz): δ= S6
7 ppm. MS m/z (rel. int.): [M+2] 427 (19), [M+] 425 (42), 386 (13), 345 (100), 306 (44), 267 (3), 242 (11), 217 (8), 119 (20). HRMS cald. for C 21 H 17 ClN 3 Se: [M + H] Found: ((3-(trifluoromethyl)phenyl)selanyl)-1,3-diphenyl-1Hpyrazol-5-amine (4o): Reddish oil; Yield: 24%; 1 H NMR (CDCl 3, 400 MHz): δ = (m, 2H), (m, 12H), 3.38 ppm (s, 2H). 13 C NMR (CDCl 3, 100 MHz): δ = 153.3, 149.5, 138.3, 134.5, 132.7, 131.8, (d, J = 32 Hz), (d, J = 1.5 Hz), 129.5, 128.2, 128.1, 127.7, (d, J = 3.9 Hz), (d, J = 272 Hz) 123.5, (d, J = 3.9 Hz), 81.5 ppm. MS m/z (rel. int.): 459 (44), 457 (22), 379 (100), 358 (3), 341 (4), 281 (12), 253 (5), 207 (35), 180 (3), 132 (24), 119 (22), 77 (57). (E)-1,2-bis(1,3-diphenyl-4-(phenylselanyl)-1Hpyrazol-5-yl)diazene (6): Reddish solid; m.p.: C; Yield: 50%; 1 H NMR (CDCl 3, 400 MHz): δ= (m, 4H), (m, 24H), ppm (m, 2H). 13 C NMR (CDCl 3, 100 MHz): δ= 151.1, 138.8, 131.6, 130.9, 129.6, 129.4, 129.3, 129.2, 129.2, 128.9, 128.7, 128.4, 128.2, 125.9, 125.8, 124.9, 124.5, MS m/z (rel. int.): 778 (3), 621 (10), 541 (30), 311 (13), 169 (10), 155 (11), 91 (16), 77 (100). Reference: 1. Jiang, B.; Ning, Y.; Fan, W.; Tu, S. J.; Li, G. J. Org. Chem. 2014, 79, S7
8 Table S1. Crystallographic data and refinement parameters for 6. Crystal Data 6 Formula C 42 H 30 N 6 Se 2 Fw (g mol -1 ) T (K) 100(2) Crystal system Monoclinic Space group P2 1 /c a/å (4) b/å (11) c/å (3) / 90 / (10) / 90 V/Å (2) Z 4 D calc (g cm -3 ) μ (Mo Kα) (mm 1 ) λ/å F (000) 1568 Collected reflns Unique reflns Goof (F 2 ) R 1 a wr 2 b a R 1 = IIFoI - IFcII / IFoI. b wr 2 = { w(f o 2 - F c 2 ) 2 / w(f o 2 ) 2 } 1/2. S8
9 SELECTED SPECTRA Figure S1. 1 H NMR (400 MHz, CDCl 3 ) of the product 4a. S9
10 Figure S2. 13 C NMR (100 MHz, CDCl 3 ) of the product 4a. S10
11 Figure S3. 1 H NMR (400 MHz, CDCl 3 ) of the product 4b. S11
12 Figure S4. 13 C NMR (100 MHz, CDCl 3 ) of the product 4b. S12
13 Figure S5. 1 H NMR (400 MHz, CDCl 3 ) of the product 4b. S13
14 Figure S6. 13 C NMR (100 MHz, CDCl 3 ) of the product 4c. S14
15 Figure S7. 1 H NMR (400 MHz, CDCl 3 ) of the product 4d. S15
16 Figure S8. 13 C NMR (100 MHz, CDCl 3 ) of the product 4d. S16
17 Figure S9. 1 H NMR (400 MHz, CDCl 3 ) of the product 4e. S17
18 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4e. S18
19 Figure S11. 1 H NMR (400 MHz, CDCl 3 ) of the product 4g. S19
20 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4g. S20
21 Figure S13. 1 H NMR (400 MHz, CDCl 3 ) of the product 4h. S21
22 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4h. S22
23 Figure S15. 1 H NMR (400 MHz, CDCl 3 ) of the product 4i. S23
24 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4i. S24
25 Figure S17. 1 H NMR (400 MHz, CDCl 3 ) of the product 4j. S25
26 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4j. S26
27 Figure S19. 1 H NMR (400 MHz, CDCl 3 ) of the product 4l. S27
28 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4l. S28
29 Figure S21. 1 H NMR (400 MHz, CDCl 3 ) of the product 4m. S29
30 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4m. S30
31 Figure S23. 1 H NMR (400 MHz, CDCl 3 ) of the product 4n. S31
32 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4n. S32
33 Figure S25. 1 H NMR (400 MHz, CDCl 3 ) of the product 4o S33
34 Figure S C NMR (100 MHz, CDCl 3 ) of the product 4o. S34
35 Figure S27. 1 H NMR (400 MHz, CDCl 3 ) of the product 6. S35
36 Figure S C NMR (100 MHz, CDCl 3 ) of the product 6. S36
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