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  • Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz
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Supplementary Information S I J. Braz. Chem. Soc., Vol. 24, No. 2, S1-S19, 2013. Printed in Brazil - ©2013 Sociedade Brasileira de Química 0103 - 5053 $6.00+0.00 *e-mail: [email protected] Synthesis of Novel Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions Bianca N. M. Silva,* ,a Bárbara V. Silva, a Fernando C. Silva, b Daniel T. G. Gonzaga, b Vitor F. Ferreira b and Angelo C. Pinto a a Instituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro-RJ, Brazil b Instituto de Química, Universidade Federal Fluminense, 24020-141 Niterói-RJ, Brazil Experimental Typical procedure for preparation of 5-nitro-spiro[1,3- dioxolane-2,3’-indol]-2’(1’H)-one (8) A mixture of 5-nitro-isatin (6.8 mmol), ethylene glycol (108 mmol), p-toluenesulfonic acid (0.58 mmol) and toluene (15 mL) was refluxed in a round bottom flask connected to a Dean-Stark apparatus. 5-Nitro-spiro[1,3- dioxolane-2,3’-indol]-2’(1’H)-one was obtained after 6 h of reaction. After this period, the crude reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried with anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. Typical procedure for preparation of 5-amine-spiro[1,3- dioxolane-2,3’-indol]-2’(1’H)-one (9) To appropriate glass bottle, it was added 40 mL of ethyl acetate, 0.091 g of charcoal-supported palladium (10%) and 2 mmol of 5-nitro-spiro[1,3-dioxolane- 2,3’-indol]-2’(1’H)-one. The flask was properly conditioned using a PARR hydrogenator at 35 psi. After 1 h, the reaction medium was filtered and the solvent was evaporated under reduced pressure. Typical procedure for preparation of 5-azido-spiro[1,3- dioxolane-2,3’-indol]-2’(1’H)-one (10) A solution containing 7 mmol of sodium nitrite dissolved in 13 mL of water was prepared and poured into another solution containing 5 mmol of 5-amino-spiro[1,3- dioxolane-2,3’-indol]-2’(1’H)-one in 5 mL of 6 mol L -1 HCl. After the reaction, it was kept at 0-5 °C for 30 min, a solution of sodium azide (19.5 mmol) in 26 mL of water was added dropwise. After 4 h of stirring, the mixture was neutralized with sodium bicarbonate and filtered under reduced pressure. Typical procedure for preparation of 5’-(4-alquil/aril- 1H-1,2,3-triazole)-isatin (11a-11l) A mixture of 2.64 mmol of 5-azido-spiro[1,3-dioxolane- 2,3’-indol]-2’(1’H)-one, 3.17 mmol of the alkyne (see Scheme 1), 0.19 mmol of CuSO 4 .5H 2 O, an excess of AscNa (0.42 mmol), 0.87 mmol (30 mol% based on 10) of acetic acid and an equal amount of tert-butanol and water (2.24 mL) was allowed to stir at room temperature for 24 h. After this period, liquid-liquid extraction was performed with ethyl acetate and water. The organic layer was dried with anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure.

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Page 1: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Supplementary Information SIJ. Braz. Chem. Soc., Vol. 24, No. 2, S1-S19, 2013.

Printed in Brazil - ©2013 Sociedade Brasileira de Química0103 - 5053 $6.00+0.00

*e-mail: [email protected]

Synthesis of Novel Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Bianca N. M. Silva,*,a Bárbara V. Silva,a Fernando C. Silva,b Daniel T. G. Gonzaga,b Vitor F. Ferreirab and Angelo C. Pintoa

aInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro-RJ, Brazil

bInstituto de Química, Universidade Federal Fluminense, 24020-141 Niterói-RJ, Brazil

Experimental

Typical procedure for preparation of 5-nitro-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one (8)

A mixture of 5-nitro-isatin (6.8 mmol), ethylene glycol (108 mmol), p-toluenesulfonic acid (0.58 mmol) and toluene (15 mL) was refluxed in a round bottom flask connected to a Dean-Stark apparatus. 5-Nitro-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one was obtained after 6 h of reaction. After this period, the crude reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried with anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure.

Typical procedure for preparation of 5-amine-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one (9)

To appropriate glass bottle, it was added 40 mL of ethyl acetate, 0.091 g of charcoal-supported palladium (10%) and 2 mmol of 5-nitro-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one. The flask was properly conditioned using a PARR hydrogenator at 35 psi. After 1 h, the reaction medium was filtered and the solvent was evaporated under reduced pressure.

Typical procedure for preparation of 5-azido-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one (10)

A solution containing 7 mmol of sodium nitrite dissolved in 13 mL of water was prepared and poured into another solution containing 5 mmol of 5-amino-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one in 5 mL of 6 mol L-1 HCl. After the reaction, it was kept at 0-5 °C for 30 min, a solution of sodium azide (19.5 mmol) in 26 mL of water was added dropwise. After 4 h of stirring, the mixture was neutralized with sodium bicarbonate and filtered under reduced pressure.

Typical procedure for preparation of 5’-(4-alquil/aril-1H-1,2,3-triazole)-isatin (11a-11l)

A mixture of 2.64 mmol of 5-azido-spiro[1,3-dioxolane-2,3’-indol]-2’(1’H)-one, 3.17 mmol of the alkyne (see Scheme 1), 0.19 mmol of CuSO4.5H2O, an excess of AscNa (0.42 mmol), 0.87 mmol (30 mol% based on 10) of acetic acid and an equal amount of tert-butanol and water (2.24 mL) was allowed to stir at room temperature for 24 h. After this period, liquid-liquid extraction was performed with ethyl acetate and water. The organic layer was dried with anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure.

Page 2: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S2

11a. HRMS ESI+ [M + H]+. found 335.1134, C18H15N4O3+ requires 335.1139; IR (KBr)

νmax/cm-1 3291, 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz, DMSO-d6) d 10.80 (s, 1H, NH); 9.25 (s, 1H, H10); 7.95-7.93 (m, 4H); 7.49 (t, 2H, J 8 Hz); 7.37 (t, 1H, J 8 Hz); 7.08 (d, 1H, J 8 Hz, H7); 4.42-4.32 (m, 4H, H8 and H9); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 147.6 (Cq); 143.4 (Cq); 132.4 (Cq); 130.7 (Cq); 129.4 (CH); 128.6 (CH); 126.5 (Cq); 125.7 (CH); 124.2 (Cq); 120.1 (CH); 117.8 (CH); 111.9 (CH); 111.9 (CH); 101.7 (Cq); 66.2 (CH2); mp 230 ºC.

Figure S1. 1H NMR spectrum (500 MHz, DMSO) of compound 11a.

Figure S2. 13C NMR spectrum (500 MHz, DMSO) of compound 11a.

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Silva et al. S3Vol. 24, No. 2, 2013

Figure S3. IR spectrum (KBr) of compound 11a.

11b. HRMS ESI+ [M + H]+. found 289.0936, C13H13N4O4+ requires 289.0931; IR (KBr)

νmax/cm-1 3443, 3143, 2968, 1727, 1635, 1508, 1473, 1289, 1149, 994, 844 and 547; 1H RMN (400 MHz, DMSO-d6) d 10.74 (s, 1H, NH); 8.64 (s, 1H, H10); 7.89-7.87 (m, 2H, H4 and H6); 7, 02 (d, J 8 Hz, 1H, H7); 5.34 (t, J 8Hz, OH); 4.61 (d, J 8 Hz, 2H, H12); 4.39-4.30 (m, 4H, H8 and H9); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 149.4 (Cq); 143.1 (Cq); 132.5 (CH); 126.6 (Cq); 124.0 (CH); 121.4 (CH); 117.7 (CH); 111.8 (CH); 101.7 (Cq); 66.2 (CH2); 55.4 (CH2); mp 225 ºC.

Figure S4. 1H NMR spectrum (500 MHz, DMSO) of compound 11b.

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Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S4

Figure S5. 13C NMR spectrum (500 MHz, DMSO) of compound 11b.

Figure S6. IR spectrum (KBr) of compound 11b.

11c. HRMS ESI+ [M + H]+. found 317.1238, C15H17N4O4+ requires 317.1244; IR (KBr)

νmax/cm-1 3461, 2979, 1727, 1631, 1508, 1286, 1158, 1080, 837, 723 and 554; 1H RMN (400 MHz, DMSO-d6) d 10.7 (sl, 1H, NH); 8.56 (s, 1H, H10); 7.90-7.88 (m, 2H, H4 and H6); 7.02 (d, 1H, J 12 Hz, H7); 5.23 (sl, 1H, OH); 4.39-4.30 (m, 4H, H8 and H9); 1.53 (s, 6H, H13 and H14); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 157.1 (Cq), 143.0 (Cq); 132.6 (Cq); 132.6 (CH); 126.6 (Cq); 119.3 (CH); 117.6 (CH); 111.8 (CH); 101.7 (CH); 67.3 (Cq); 66.2 (CH2); 30.9 (CH2); mp 132 ºC.

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Silva et al. S5Vol. 24, No. 2, 2013

Figure S8. 13C NMR spectrum (500 MHz, DMSO) of compound 11c.

Figure S9. IR spectrum (KBr) of compound 11c.

Figure S7. 1H NMR spectrum (500 MHz, DMSO) of compound 11c.

Page 6: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S6

11d. HRMS ESI+ [M + H]+. found 331.1407, C16H19N4O4+ requires 331.1401; IR (KBr)

νmax/cm-1 3485, 2973, 1734, 1631, 1504, 1293, 1215, 1143, 1052, 754 and 545; 1H RMN (400 MHz, DMSO-d6) d 10. 72 (sl, 1H, NH); 8.53 (sl, 1H, H10); 7.90-7.88 (m, 2H, H4 and H6); 7.01 (d, 1H, J 8 Hz, H7); 5.07 (s, 1H, OH); 4.38-4.30 (m, 4H, H8 and H9); 1.79 (q, J 8 Hz, 2H, H12); 1.49 (s, 1H, H14); 0.79 (t, 3H, J 8 Hz, H13); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 156.1 (Cq); 142.9 (Cq); 132.6 (Cq); 126.7 (Cq); 123.8 (CH); 119.9 (CH); 119.9 (CH), 117.5 (CH); 111.8 (CH); 109.9 (Cq); 101.7 (Cq); 70.1 (CH2); 66.2 (CH2); 35.7 (CH3); 28.4 (CH3); mp 92 ºC.

Figure S10. 1H NMR spectrum (500 MHz, DMSO) of compound 11d.

Figure S11. 13C NMR spectrum (500 MHz, DMSO) of compound 11d.

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Silva et al. S7Vol. 24, No. 2, 2013

Figure 12S. IR spectrum (KBr) of compound 11d.

Figure S13. 1H NMR spectrum (500 MHz, DMSO) of compound 11e.

11e. HRMS ESI+ [M + H found 357.1561, C18H21N4O4+ requires 357.1557; IR

(KBr) νmax/cm-1 3268, 3104, 2931, 1754, 1632, 1498, 1279, 970, 896 and 605; 1H RMN (400 MHz, DMSO-d6) d 10.72 (sl, 1H, NH); 8.58 (s, 1H, H10); 7.90-7.88 (m, 2H, H4 and H6); 7.01 (d, 1H, J 12 Hz, H7); 4.97 (s, 1H, OH), 4.39-4.30 (m, 4H, H8 and H9); 4.05-4.00 (q, 2H, J 8 Hz), 1.98-1.91 (m, 4H), 1.79-1.68 (m, 4H), 1.17 (t, 2H, J 8 Hz); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 156.9 (Cq); 143.0 (Cq); 132.6 (Cq); 132.6 (Cq); 126.6 (Cq), 123.8 (CH); 119.7 (CH); 119.7 (CH), 117.5 (CH); 111.8 (CH); 101.7 (Cq); 68.3 (CH2); 25.6 (CH2); 22.1 (CH2); 14.5 (CH3); mp 188 ºC.

Page 8: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S8

Figure S14. 13C NMR spectrum (500 MHz, DMSO) of compound 11e.

Figure S15. IR spectrum (KBr) of compound 11e.

11f. HRMS ESI+ [M + H]+. found 341.1602, C18H21N4O3+ requires 341.1608; IR (KBr)

νmax/cm-1 3313, 3148, 2924, 1755, 1630, 1267, 1218, 1063, 996, 825, 726 and 550; 1H RMN (400 MHz, DMSO-d6) d 10.71 (s, 1H, NH); 8.50 (s, 1H, H10); 7.86-7.84 (m, 2H, H4 and H6); 7.01 (d, 1H, J 8 Hz, H7); 4.39-4.30 (m, 4H, H8 and H9); 2.72 (qt, 1H, H12); 2.02-2.00 (m, 2H); 1.91 (sl, 3H); 1.77-1.74 (m, 3H); 1.48-1.36 (m, 4H); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 172.4 (Cq); 153.6 (Cq); 142.9 (Cq); 132.6 (Cq); 126.5 (Cq); 123.8(CH); 119.3 (CH); 117.5 (CH); 111.8 (CH); 109.9 (CH2); 101.7(CH2); 66.2 (CH2); 35.0 (CH); 32.8 (CH2); 25.9 (CH2); 25.9 (CH2); 21.4 (CH2); mp 180 ºC.

Page 9: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Silva et al. S9Vol. 24, No. 2, 2013

Figure S17. 13C NMR spectrum (500 MHz, DMSO) of compound 11f.

Figure S16. 1H NMR spectrum (500 MHz, DMSO) of compound 11f.

Page 10: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S10

Figure S18. IR spectrum (KBr) of compound 11f.

11g. HRMS ESI+ [M + H]+. found 339.1447, C18H19N4O3+ requires 339.1452; IR

(KBr) νmax/cm-1 3197, 3163, 2935, 1742, 1628, 1505, 1277, 1056, 954, 777 and 728; 1H RMN (400 MHz, DMSO-d6) d 10. 75 (s, 1H, NH); 8.73 (s, 1H, H10); 7.89-7.87 (m, 2H, H4, H6); 7.03 (d, 1H, J 8 Hz, H7); 6.51 (sl, 1H, H11); 4.40-4.30 (m, 4H, H8 and H9); 2.38 (m, 2H); 2.17 (m, 2H); 1.66 (m, 4H); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 149.3 (Cq); 143.1 (Cq); 132.5 (Cq); 127.6 (Cq); 126.5 (Cq); 124.6 (CH); 123.9 (CH); 118.4 (CH); 117.5 (CH); 111.8 (CH); 101.7 (Cq); 66.2 (CH2); 26.2 (CH2); 25.1 (CH2); 22.4 (CH2); 22.2 (CH2); mp 227 ºC.

Figure S19. 1H NMR spectrum (500 MHz, DMSO) of compound 11g.

Page 11: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Silva et al. S11Vol. 24, No. 2, 2013

Figure S20. 13C NMR spectrum (500 MHz, DMSO) of compound 11g.

Figure S21. IR spectrum (KBr) of compound 11g.

11h. HRMS ESI+ [M + H]+. found 329.1615, C17H21N4O3+ requires 329.1608; IR (KBr)

νmax/cm-1 3336, 3111, 2952, 1747, 1632, 1505, 1282, 944, 751 and 546; 1H RMN (400 MHz, DMSO-d6) d 10.74 (sl, 1H, NH); 8.50 (s, 1H, H10); 7.85-7.83 (m, 2H, H4 and H6); 7.00 (d, 1H, J 8 Hz, H7); 4.38-4.29 (m, 4H, H8 and H9); 2.66 (t, 2H, J 8 Hz, H12); 1.64 (qt, 2H, J 8Hz, H13); 1.32-1.31 (m, 4H, H14 and H15); 0.86 (t, 3H, J 4 Hz, H16); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 148.5 (Cq); 143.0 (Cq); 132.6 (Cq); 126.5 (Cq); 123.9 (CH); 120.5 (CH); 117.5 (CH); 111.8 (CH); 101.7 (Cq); 66.2 (CH2); 31.2 (CH2); 28.8 (CH2); 25.3 (CH2); 22.3 (CH2); 14.3 (CH3); mp 112 ºC.

Page 12: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S12

Figure S22. 1H NMR spectrum (500 MHz, DMSO) of compound 11h.

Figure S23. 13C NMR spectrum (500 MHz, DMSO) of compound 11h.

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Silva et al. S13Vol. 24, No. 2, 2013

Figure S24. IR spectrum (KBr) of compound 11h.

11i. HRMS ESI+ [M + H]+. found 315.1455. C16H19N4O3+ requires 315.1452; IR

(KBr) νmax/cm-1 3316, 2927, 1751, 1633, 1506, 1221, 1091, 1034, 947 and 838; 1H RMN (400 MHz, DMSO-d6) d 10.72 (s, 1H, NH); 8.53 (s, 1H, H10); 7.86-7.84 (m, 2H, H4 and H6); 6.99 (d, 1H, J 8 Hz, H7); 4.37-4.28 (m, 4H, H8 and H9); 2.68 (t, 2H, J 8 Hz, H12); 1.63 (qt, 2H, J 8 Hz, H13); 1.36 (sext, 2H, J 8Hz, H14); 0.91 (t, 3H, J 8Hz, H15); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 143.0 (Cq); 132.6 (Cq); 126.5 (Cq); 123.8 (CH); 120.6 (CH); 117.5 (CH); 111.8 (CH); 109.9 (Cq); 101.7 (Cq); 66.2 (CH2); 31.3 (CH2); 25.1 (CH2); 22.1 (CH2); 14.1 (CH3); mp 127 ºC.

Figure S25. 1H NMR spectrum (500 MHz, DMSO) of compound 11i.

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Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S14

Figure S26. 13C NMR spectrum (500 MHz, DMSO) of compound 11i.

Figure S27. IR spectrum (KBr) of compound 11i.

11j. HRMS ESI+ [M + H]+. found 301.1289, C15H17N4O3+ requires 301.1295; IR

(KBr) νmax/cm-1 3315, 3076, 2960, 1748, 1633, 1507, 1223, 1081, 947, 838 and 545; 1H RMN (400 MHz, DMSO-d6) d 10.73 (sl, 1H, NH); 8.52 (s, 1H, H10); 7.86-7.84 (m, 2H, H4 and H6); 7.02 (d, 1H, J 12 Hz, H7); 4.39-4.30 (m, 4H, H8 and H9); 2.66 (t, 2H, J 8 Hz, H12); 1.67 (sext, 2H, J 8Hz, H13); 0.94 (t, 3H, J 8 Hz, H14); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 148.3 (Cq); 143.0 (Cq); 132.6 (Cq); 126.5 (Cq); 123.9 (CH); 120.6 (CH); 117.6 (CH); 111.8 (CH); 101.7 (Cq); 66.2 (CH2); 27.5 (CH2); 22.5 (CH2); 14.0 (CH3); mp 181 ºC.

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Silva et al. S15Vol. 24, No. 2, 2013

Figure S28. 1H NMR spectrum (500 MHz, DMSO) of compound 11j.

Figure S29. 13C NMR spectrum (500 MHz, DMSO) of compound 11j.

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Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S16

Figure S30. IR spectrum (KBr) of compound 11j.

11k. HRMS ESI+ [M + H]+. found 331.1026, C15H15N4O5+ requires 331.1037;

IR (KBr) νmax/cm-1 3154, 2899, 1748, 1632, 1507, 1217, 1038, 998, 730 and 543 1H RMN (400 MHz, DMSO-d6) d 10.74 (s, 1H, NH); 8.79 (s, 1H, H10); 7.88-7.86 (m, 2H, H4 and H6); 7.03 (d, 1H, J 8 Hz, H7); 5.20 (s, 2H, H12); 4.39-4.31 (m, 4H, H8 and H9); 2.06 (sl, 3H, H14); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 170.5 (Cq); 143.4 (Cq); 143.4 (Cq); 132.2 (Cq); 126.6 (Cq); 124.3 (CH); 123.3 (CH); 118.6 (CH); 111.8 (CH); 101.7 (Cq); 66.2 (CH2); 57.4 (CH2); 21.0 (CH3); mp 171 ºC.

Figure S31. 1H NMR spectrum (500 MHz, DMSO) of compound 11k.

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Silva et al. S17Vol. 24, No. 2, 2013

Figure S32. 13C NMR spectrum (500 MHz, DMSO) of compound 11k.

Figure S33. IR spectrum (KBr) of compound 11k.

11l. HRMS ESI+ [M + H]+. found 317.1242, C15H17N4O4+ requires

317.1244; IR (KBr) νmax/cm-1 3211, 2945, 1747, 1635, 1509, 1271, 1192, 1090, 988, 735 and 544; 1H RMN (400 MHz, DMSO-d6) d 10.73 (s, 1H, NH); 8.53 (s, 1H, H10); 7.86-7.84 (m, 2H, H4, H6); 7.02 (d, 1H, J 8 Hz, H7); 4.55-4.53 (m, 1H, H14); 4.39-4.30 (m, 4H, H8 and H9); 3.76-3.66 (m, 3H); 2.76 (t, 2H); 1.91 (quint, 2H), 1.72-1.59 (m, 4H); 13C RMN (100 MHz, DMSO-d6) d 174.7 (Cq); 148.0 (Cq); 143.0 (Cq); 132.6 (Cq); 126.5 (Cq); 123.8 (CH); 120.6 (CH); 117.6 (CH); 111.8 (CH); 109.9 (CH); 101.7 (Cq); 98.4 (CH2); 66.2 (CH2); 61.7 (CH); 30.7 (CH2); 29.3 (CH2); 25.4 (CH2); 22.3 (CH2); 19.6 (CH2); mp 121 ºC.

Page 18: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Synthesis of Novel Isatin-Type 5’-(4-alkyl/aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions J. Braz. Chem. Soc.S18

Figure S34. 1H NMR spectrum (500 MHz, DMSO) of compound 11l.

Figure S35. 13C NMR spectrum (500 MHz, DMSO) of compound 11l.

Page 19: Supplementary Information J. Braz. Chem. Soc. SI · Supplementary Information SI J. Braz. Chem. Soc ... 1736, 1637, 1508, 1470, 1292, 1213, 1077, 762, 553 and 507; 1H RMN (400 MHz

Silva et al. S19Vol. 24, No. 2, 2013

Figure S36. IR spectrum (KBr) of compound 11l.


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