General procedure J for the synthesis of polymer by employing malonic acid via

A Schlenk tube was charged with furfural (83 μL, 1 mmol), malonic acid (52.03 mg, 0.5 mmol), ethylenediamine (34 μL, 0.5 mmol), dissolved in MeOH (2 mL) and sealed with a suba.

The solution was stirred for 2 h at room temperature. Then was added tert-butyl isocyanide (0,12 mL, 1 mmol) to the solution and stirred for 4 days. Next, the solution was concentrated in vacuo and subsequently was dissolved with a slightly quantity of dichloromethane, and next with petroleum ether.

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2

A

A ^PPENDIX

Spectrum 6. ¹H-NMR spectrum of compound 3.1.1.

Spectrum 7. ¹³C-NMR spectrum of compound 3.1.1.

Spectrum 8. IR spectrum of compound 3.1.1.

4

Spectrum 9. ¹H NMR spectrum of bis(1-phenyl)ether.

Spectrum 10. ¹³H-NMR spectrum of compound 5.1.1.

Spectrum 11. ¹³C-NMR spectrum of compound 5.1.1.

Spectrum 12. IR spectrum of compound 5.1.1.

6

Spectrum 13.¹H-NMR spectrum of compound 10.

Spectrum 14. ¹H-NMR spectrum of compound 4.3.

Spectrum 15. ¹H-NMR spectrum of compound 3.1.2.

Spectrum 16. ¹³C-NMR spectrum of compound 3.1.2.

8

Spectrum 17. IR spectrum of compound 3.1.2.

Spectrum 18. ¹H-NMR spectrum of compound 3.1.3.

Spectrum 19.¹³C-NMR spectrum of compound 3.1.3.

Spectrum 20. IR spectrum of compound 3.1.3.

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Spectrum 21. ¹H-NMR spectrum of compound 3.1.4.

Spectrum 22. ¹³C-NMR spectrum of compound 3.1.4.

Spectrum 23. IR spectrum of compound 3.1.4.

Spectrum 24. ¹H-NMR spectrum of compound 3.1.5.

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Spectrum 25. ¹³C-NMR spectrum of compound 3.1.5.

Spectrum 26. IR spectrum of compound 3.1.5.

Spectrum 27. ¹H-NMR of compound 3.1.6.

Spectrum 28. ¹³C-NMR of compound 3.1.6.

14

Spectrum 29. IR spectrum of compound 3.1.6.

Spectrum 30. m/z spectrum of compound 3.1.6.

G:\My Drive\...\MMM_UNL\JP76_100uM_ACN 7/15/2022 7:47:39 PM

JP76_100uM_ACN #70-149 RT:0.44-0.89 AV:80 NL:1.18E7 T:FTMS + p ESI Full ms [50.0000-750.0000]

268 269 270 271 272 273 274 275 276 277 278 279 280 281

m/z 0

10 20 30 40 50 60 70 80 90 100

Relative Abundance

274.0984

276.0956

275.1018

277.0989

Spectrum 31. ¹H-NMR spectrum of compound 3.1.7.

Spectrum 32. ¹³C-NMR spectrum of compound 3.1.7.

16

Spectrum 33. IR spectrum of compound 3.1.7.

Spectrum 34. m/z spectrum of compound 3.1.7.

G:\My Drive\...\MMM_UNL\JP77_100uM_ACN 7/15/2022 7:40:56 PM

JP77_100uM_ACN #76-152 RT:0.47-0.89 AV:77 NL:2.81E7 T:FTMS + p ESI Full ms [50.0000-750.0000]

245 250 255 260 265 270

m/z 0

10 20 30 40 50 60 70 80 90 100

Relative Abundance

254.1531

255.1564

256.1597

Spectrum 35. ¹H-NMR spectrum of compound 3.2.1.

Spectrum 36. ¹³C-NMR spectrum of compound 3.2.1.

18

Spectrum 37. IR spectrum of compound 3.2.1.

Spectrum 38. ¹H-NMR spectrum of compound 3.3.1.

Spectrum 39. ¹³C-NMR spectrum of compound 3.3.1.

Spectrum 40. ¹H-NMR spectrum of compound 3.4.1.

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Spectrum 41. ¹³C-NMR spectrum of compound 3.4.1.

Spectrum 42. IR spectrum of compound 3.4.1.

Spectrum 43. m/z spectrum of compound 3.4.1.

Spectrum 44. ¹H-NMR spectrum of compound 3.5.1.

G:\My Drive\...\MMM_UNL\JP73_100uM_ACN 7/15/2022 7:34:15 PM

JP73_100uM_ACN #70-138 RT:0.44-0.82 AV:69 NL:2.30E7 T:FTMS + p ESI Full ms [50.0000-750.0000]

162 164 166 168 170 172 174 176 178 180 182 184

m/z 0

10 20 30 40 50 60 70 80 90 100

Relative Abundance

168.0652

169.0685

22

Spectrum 45. ¹³C-NMR spectrum of compound 3.5.1.

Spectrum 46. IR spectrum of compound 3.5.1.

Spectrum 47. ¹H-NMR spectrum of compound 14.2.

Spectrum 48. ¹³C-NMR spectrum of compound 14.2.

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Spectrum 49. FTIR spectrum of compound 14.2.

Spectrum 50. m/z spectrum of compound 14.2.

D:\HRMS\JP64_100uM_ACN_20220719172151 7/19/2022 5:23:10 PM

JP64_100uM_ACN_20220719172151 #93-152 RT:0.57-0.88 AV:60 NL:1.01E8 T:FTMS + p ESI Full ms [50.0000-750.0000]

250 260 270 280 290 300 310 320 330 340 350 360

m/z 0

10 20 30 40 50 60 70 80 90 100

Relative Abundance

281.1851

303.1669

319.1407 283.1913

255.2423

305.1733

26

No documento Expedient synthesis of amides: application of biomass-derived catalysts and multicompo-nent reactions (páginas 105-139)