Ugi-Smiles couplings in water

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 4962-4964

  Kaïm, Laurent El ^a   Grimaud, Laurence ^a   Purumandla, Srinivas Reddy ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; CYANIDE; METHANOL; PHENOL; TOLUENE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; REACTION ANALYSIS; TEMPERATURE; UGI SMILES REACTION;

EID: 78549231563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.058     Document Type: Article

References (31)

1. Ugi, I.; Meyr, R.; Fetzer, U.; Steinbrückner, C. Angew. Chem. 1959, 71, 386;
2. Ugi, I.; Steinbrückner, C. Angew. Chem. 1960, 72, 267-268.
3. For recent reviews, see: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210;
4. Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329;
5. Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66
6. Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313;
7. Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005;
8. Dömling, A. Chem. Rev. 2006, 106, 17-89.
9. El Kaim, L.; Grimaud, L.; Oble, J. Angew. Chem., Int. Ed. 2005, 117, 7961-7964;
10. El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem. 2007, 72, 4169-4180;
11. El Kaïm, L.; Grimaud, L. Mol. Divers. 2009. doi:10.1007/s11030-009- 9175-3.
12. El Kaïm, L.; Grimaud, L.; Oble, J. J. Org. Chem. 2007, 72, 5835-5838;
13. Oble, J.; El Kaïm, L.; Gizzi, M.; Grimaud, L. Heterocycles 2007, 73, 503-517;
14. El Kaim, L.; Gizzi, M.; Grimaud, L. Org. Lett. 2008, 10, 3417-3419;
15. Coffinier, D.; El Kaim, L.; Grimaud, L. Org. Lett. 2009, 11, 995-997;
16. El Kaïm, L.; Gamez-Montano, R.; Grimaud, L.; Ibarra-Rivera, T. Chem. Commun. 2008, 11, 1350-1352.
17. 4), concentrated and the residue was purified by flash chromatography on silica gel (EtOAc/PE, 1:2) to give the desired adduct (300 mg, 77%).
18. 3, 400 MHz) δ 7.65 (dd, 1H, J = 1.5, 8.1 Hz), 7.48 (dt, 1H, J = 1.5, 8.1 Hz), 7.38 (t, 1H, J = 5.3 Hz), 7.27-7.22 (m, 3H), 7.18-7.10 (m, 3H), 5.65-5.55 (m, 1H), 5.08-5.01 (m, 2H), 4.44 (dd, 1H, J = 6.1, 14.9 Hz), 4.36 (dd, 1H, J = 6.1, 14.9 Hz), 3.82-3.77 (m, 1H), 3.74 (d, 1H, J = 6.1 Hz), 3.51 (dd, 1H, J = 6.3, 15.4 Hz), 2.05-1.94 (m, 1H), 1.83-1.72 (m, 1H), 0.95 (t, 3H, J = 7.6 Hz);
19. l3, 100.6 MHz) δ 172.0, 146.3, 143.0, 137.3, 133.4, 133.3, 132.9, 129.5, 129.0, 125.6, 125.5, 124.2, 119.6, 68.5, 53.6, 43.1, 23.4, 11.5;
20. 3: 387.1350, found 387.1329.
21. Oble, J.; El Kaïm, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 4019-4021;
22. Barthelon, A.; Dos Santos, A.; El Kaim, L.; Grimaud, L. Tetrahedron Lett. 2008, 49, 3208-3211.
23. El Kaïm, L.; Gizolme, M.; Grimaud, L. Synlett 2007, 465-469;
24. Barthelon, A.; El Kaïm, L.; Gizolme, M.; Grimaud, L. Eur. J. Org. Chem. 2008, 35, 5974-5987
25. 4), concentrated in vacuo and the residue was purified by flash chromatography on silica gel (EtOAc/PE, 1:9) to give the desired adduct (170 mg, 41%).
26. l3, 400 MHz) δ 9.78 (br s, 1H), 7.64 (d, 1H, J = 7.8 Hz), 7.43 (d, 1H, J = 8.0 Hz), 7.39-7.27 (m, 6H), 7.13 (t, 1H, J = 7.4 Hz), 6.17 (s, 1H), 5.95-5.85 (m, 1H), 5.32 (dd, 1H, J = 1.3, 17.2 Hz), 5.26 (dd, 1H, J = 1.0, 10.1 Hz), 4.50-4.40 (m, 1H), 4.29 (dd, 1H, J = 5.4, 16.3 Hz), 4.21 (dd, 1H, J = 5.4, 16.3 Hz), 2.20-2.12 (m, 1H), 2.01-1.93 (m, 1H), 1.79-1.70 (m, 1H), 1.66- 1.57 (m, 2H), 1.52-1.33 (m, 3H), 1.28-1.15 (m, 2H);
27. l3, 100.6 MHz) δ 198.1, 168.1, 151.6, 136.1, 132.5, 131.2, 128.9, 128.6, 128.5, 126.4, 122.3, 121.2, 120.1, 119.5, 77.1, 56.6, 54.7, 31.4, 31.3, 25.9, 24.74, 24.67;
28. -1;
29. 2: 421.1646, found 421.1658.
30. Pirrung, M. C.; Das Sarma, K. J. Am. Chem. Soc. 2004, 126, 444-445.
31. Acceleration of Passerini reactions has been studied by Pirrung et al. (see Ref. 3) and Mironov et al.: Mironov, M. A.; Ivantsova, M. N.; Tokareva, M. I.; Mokrushin, V. S. Tetrahedron Lett. 2005, 46, 3957-3960.