supporting information - nature...supporting information the use of the ugi four-component...

SUPPORTING INFORMATION

The use of the Ugi four-component condensation

Stefano Marcaccini1 & Tomás Torroba2

1Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via della Lastruccia, 13, I-50019 Sesto Fiorentino, Italy. 2Departamento

de Química, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain. Correspondence should be addressed to S.M.

([email protected]) (Tel. +390554573510, fax: +390554573531) or T.T. ([email protected]) (Tel. +34947258088, fax: +34947258087).

1-Cyclohexyl-5-(1-phenylamino-2-methyl)propyltetrazole (19)

Page 2: 1H-NMR (400 MHz, CDCl3)

Page 3: 1H-NMR (400 MHz, CDCl3/D2O)

Pages 4-6: COSY NMR (400 MHz, CDCl3)

Page 7: 13C-NMR (100 MHz, CDCl3)

Pages 8-9: DEPT NMR (100 MHz, CDCl3)

Pages 10-11: HMQC NMR (100 MHz, CDCl3)

N

NH

NNN

19

ppm (t1) Tetrazole, 1H

NM

R, C

DC

l3, 400 MH

z1.0

2.03.0

4.05.0

6.07.0

0 1000

2000

3000

40007.2907.2727.2467.229

4.2484.2194.190

3.7083.6893.6703.4193.385

2.1212.1052.0882.0722.053

1.9961.8811.7151.3031.2841.0761.0600.7980.782

4.79

1.23

2.14

1.29

9.26

3.18

2.97

3.00

ppm (t1) Tetrazole, CDCl3 + D2O (1H NMR 300 MHz)1.02.03.04.05.06.07.0

0

50

100

150

200

250

300

4.57

1.24

2.08

1.22

8.13

3.08

2.88

3.00

F1 (ppm)

012345678

F2(ppm)

1

2

3

4

5

6

7

8

STANDARD 1H OBSERVE

Archive directory: /export/home/vnmr1/vnmrsys/data Sample directory: File: PROTON

Pulse Sequence: gCOSY

Solvent: CDCl3 Temp. 25.0 C / 298.1 KINOVA-400 "carbono"

Relax. delay 1.000 sec Acq. time 0.156 sec Width 3286.2 Hz 2D Width 3286.2 Hz 8 repetitions 512 incrementsOBSERVE H1, 399.9389071 MHzDATA PROCESSING Sq. sine bell 0.078 secF1 DATA PROCESSING Sq. sine bell 0.156 secFT size 4096 x 4096Total time 1 hr, 25 min, 24 sec

F1 (ppm)

3.23.43.63.84.04.24.44.6

F2(ppm)

1

2

3

4

5

6

7

STANDARD 1H OBSERVE





F1 (ppm)

0.40.60.81.01.21.41.61.82.02.2

F2(ppm)

1.0

1.5

2.0

2.5

3.0

3.5

4.0

STANDARD 1H OBSERVE





ppm (t1) Tetrazole, C

DC

l3, 13C N

MR

, 100 MH

z50

100150

0 50000

10000

15000

20000

25000

30000

35000

155.116

139.092

128.418127.854127.210

77.31877.00076.682

58.29657.650

51.484

33.30233.04832.90225.27525.26324.73119.49219.335

ppm020406080100120140160180200220

13C OBSERVE

Archive directory: /export/home/vnmr1/vnmrsys/data Sample directory: File: CARBON

Pulse Sequence: DEPT


Relax. delay 1.000 sec Pulse 90.0 degrees Acq. time 2.498 sec Width 25157.2 Hz 512 repetitionsOBSERVE C13, 100.5646942 MHzDECOUPLE H1, 399.9409071 MHz Power 41 dB on during acquisition off during delay WALTZ-16 modulatedDATA PROCESSING Line broadening 1.0 HzFT size 131072Total time 30 min, 16 sec

ppm020406080100120140160180200220

13C OBSERVE

Archive directory: /export/home/vnmr1/vnmrsys/data Sample directory: File: CARBON

Pulse Sequence: DEPT


Relax. delay 1.000 sec Pulse 90.0 degrees Acq. time 2.498 sec Width 25157.2 Hz 512 repetitionsOBSERVE C13, 100.5646942 MHzDECOUPLE H1, 399.9409071 MHz Power 41 dB on during acquisition off during delay WALTZ-16 modulatedDATA PROCESSING Line broadening 1.0 HzFT size 131072Total time 2 hr, 1 min, 7 sec

F1 (ppm)

020406080100120140160180200220

F2(ppm)

1

2

3

4

5

6

7

8

STANDARD 1H OBSERVE


Pulse Sequence: gHMBC


Relax. delay 1.000 sec Acq. time 0.156 sec Width 3286.2 Hz 2D Width 24132.7 Hz 32 repetitions 512 incrementsOBSERVE H1, 399.9389071 MHzDATA PROCESSING Sine bell 0.078 secF1 DATA PROCESSING Sine bell 0.011 secFT size 1024 x 2048Total time 5 hr, 41 min, 29 sec

F1 (ppm)

020406080100120140160180

F2(ppm)

1

2

3

4

5

6

7

8

STANDARD 1H OBSERVE


Pulse Sequence: gHMQC


Relax. delay 1.000 sec Acq. time 0.156 sec Width 3286.2 Hz 2D Width 20110.6 Hz 16 repetitions 2 x 512 incrementsOBSERVE H1, 399.9389071 MHzDECOUPLE C13, 100.5737451 MHz Power 45 dB on during acquisition off during delay GARP-1 modulatedDATA PROCESSING Gauss apodization 0.072 secF1 DATA PROCESSING Gauss apodization 0.047 secFT size 1024 x 8192Total time 5 hr, 33 min, 42 sec

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