0
Dr. ANTHONY MELVIN CRASTO     PRINCIPAL SCIENTIST
MECHANISM
DRUGS
VARIATIONS
Ugi-Diels-Alder reaction
Ugi-Smiles reaction
Ugi-Buchwald-Hartwig reaction
Ugi-Heck reaction
SYNTHESIS
Ugi Reaction; N-allyl-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-3-nitropropanamide
Chemicals UsedBenzaldehyde (Acros Organics)Allylamine (Merck)Cyclohexyl isocyanide (Merck)3-Nitropropionic acid (Sigma)MeO...
   Data   IR-ATR: 3258, 3084, 2926, 2855, 1638, 1629, 1547 cm-1.    1H NMR (400 MHz, DMSO-d ): (both rotamers) ppm = 8.3...
   1-cyclohexenyl isocyanide (47 mg, 50.2 µL,0.44 mmol) was added    to a solution ofpropionic acid (33 mg, 32.9 µL,0.44 ...
   THANKS AND REGARDS    DR ANTHONY MELVIN CRASTO Ph.Damcrasto@gmail.com   MOBILE-+91 9323115463   GLENMARK SCIENTIST ...
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Anthony crasto ugi reaction
Upcoming SlideShare
Loading in...5
×

Anthony crasto ugi reaction

809

Published on

Anthony crasto presents Ugi reaction

Published in: Health & Medicine, Technology
1 Comment
0 Likes
Statistics
Notes
  • Be the first to like this

No Downloads
Views
Total Views
809
On Slideshare
0
From Embeds
0
Number of Embeds
3
Actions
Shares
0
Downloads
16
Comments
1
Likes
0
Embeds 0
No embeds

No notes for slide

Transcript of "Anthony crasto ugi reaction"

  1. 1. Dr. ANTHONY MELVIN CRASTO PRINCIPAL SCIENTIST
  2. 2. MECHANISM
  3. 3. DRUGS
  4. 4. VARIATIONS
  5. 5. Ugi-Diels-Alder reaction
  6. 6. Ugi-Smiles reaction
  7. 7. Ugi-Buchwald-Hartwig reaction
  8. 8. Ugi-Heck reaction
  9. 9. SYNTHESIS
  10. 10. Ugi Reaction; N-allyl-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-3-nitropropanamide
  11. 11. Chemicals UsedBenzaldehyde (Acros Organics)Allylamine (Merck)Cyclohexyl isocyanide (Merck)3-Nitropropionic acid (Sigma)MeOHProcedureA solution of benzaldehyde (1.70 mmol, 0.172 mL), allylamine (1.70 mmol, 0.128mL), cyclohexyl isocyanide (1.70 mmol, 0.211 mL) and 3-nitropropionicacid (1.70 mmol, 0.202 g) in 10 mL MeOH was stirred at room temperature undernitrogen atmosphere. After 28 h, the solution was concentrated under reducedpressure to leave a pale yellow solid. The residue was washed with cold Et2O (3x 20 mL) to give pure title compound as a white solid (475 mg, 75% yield, mp190-192 °C, Rf= 0.44 (ethyl acetate-hexane; 1 : 1). 1H and 13C NMR spectrashowed title compound is a mixture of two rotamers in an approximately 1:4.5ratio.
  12. 12.  Data IR-ATR: 3258, 3084, 2926, 2855, 1638, 1629, 1547 cm-1. 1H NMR (400 MHz, DMSO-d ): (both rotamers) ppm = 8.30 (0.18H, d, NH, J= 6 7.71 Hz), 8.21 (0.82H, d, NH, J= 7.71 Hz), 7.40-7.28 (3H, m, aromatic CH), 7.22 (2H, d, aromatic CH, J= 7.08 Hz), 6.12 (0.82H, s, CH-Ar), 5.65 (0.18H, s, CH- Ar), 5.45-5.37 (1H, m, CH2=CH), 5.02 (1H, appear d, CH2=CH, J=17.39 Hz), 4.95 (1H, dd, CH2=CH, J= 1.12, 10.40 Hz), 4.75-4.72 (2H, m, CH2NO2), 4.04 (2H, m, CH2=CHCH2), 3.60-3.55 (1H, m, CHNH), 3.05 (2H, t, CH2CH2NO2, J=5.23Hz), 1.75-1.62 (4H, m, cyclohexyl CH2), 1.55-1.52 (1H, m, cyclohexyl CH2), 1.30-1.04 (5H, m, cyclohexyl CH2). 13C NMR (100 MHz, DMSO-d ): (both rotamers) ppm = 170.17, 169.24, 167.95, 6 167.34, 136.47, 136.13, 134.83, 134.27, 128.80, 128.47, 128.41, 128.02, 127.84, 115.85, 115.23, 70.53, 62.28, 59.66, 47.75, 47.65, 47.31, 46.87, 32.17, 32.05, 30.03, 25.11, 24.53, 24.43. Lead Reference 1. Ugi, I.; Meyr, R. Angew. Chem., 1958, 70, 702. 2. Ugi, I.; Meyr, R. Fetzer, U. Angew. Chem., 1959, 71, 373. 3. Ugi, I.; Offermann, K. Angew. Chem. Int. Ed. Engl., 1963, 2, 624. 4. Akritopoulou-Zanze, I., Gracias, V., Moore, J. D., Djuric, S. W. Tetrahedron Lett., 2004, 45, 3421.
  13. 13.  1-cyclohexenyl isocyanide (47 mg, 50.2 µL,0.44 mmol) was added to a solution ofpropionic acid (33 mg, 32.9 µL,0.44 mmol), aniline (41 mg, 40.1 µL, 0.44 mmol), 4- phenylethylpiperidone (90 mg, 0.44 mmol) in MeOH (2.2 mL) at room temperature and the solutionwas heated at 55 C and stirred for 24 h. The solvent was removed underreduced pressure, and the residue was dissolved in EtOAc (5 mL). The organic solution was washed with sat aq NaHCO3 (2 2.5 mL) and brine (2.5 mL) and dried (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified either via HPLC/MS preparative with gradient starting from 10% MeOH / 90% H2O / 0.1% ammonia reaching 100% MeOH / 0.1%ammonia. The product was obtained in 82% yield (165 mg). Reference: Tetrahedron Letters Volume 51, Issue 22, 2 June 2010, Pages 2983-2985
  14. 14.  THANKS AND REGARDS DR ANTHONY MELVIN CRASTO Ph.Damcrasto@gmail.com MOBILE-+91 9323115463 GLENMARK SCIENTIST , NAVIMUMBAI, INDIA web link http://anthonycrasto.jimdo.com/ http://www.anthonymelvincrasto.yolasite.com/ http://www.slidestaxx.com/anthony-melvin-crasto-phd https://sites.google.com/site/anthonycrastoorganicchemistry/sites--- my-own-on-the-net http://anthonycrasto.wordpress.com/ http://organicchemistrysite.blogspot.com/ http://www.mendeley.com/profiles/anthony-melvin-crasto/ Congratulations! Your presentation titled "Anthony Crasto Glenmark scientist, helping millions with websites" has just crossed MILLION views.
  1. A particular slide catching your eye?

    Clipping is a handy way to collect important slides you want to go back to later.

×