Regio- and diastereoselective synthesis of β-lactam-triazole hybrids via passerini/CuAAC sequence

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6917-6928

  Alcaide, Benito ^a   Almendros, Pedro ^b   Aragoncillo, Cristina ^a   Callejo, Ricardo ^a   Ruiz, M Pilar ^a   Torres, M Rosario ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE SYNTHESIS; FUNCTIONALIZED; HIGH YIELD; ISOCYANIDES; REGIOSELECTIVE SYNTHESIS;

AMIDES; CARBOXYLIC ACIDS; CYANIDES; PHENOLS;

STEREOSELECTIVITY;

BETA LACTAM DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PASSERINI REACTION; PASSERINI SMILES REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84865226438     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301113g     Document Type: Article

References (56)

1. Synthesis of Heterocycles via Multicomponent Reactions I and II; Orru, R. V. A. and Ruijeter, E., Eds.; Springer-Verlag: Berlin-Heidelberg, 2010.
2. Ganem, B. Acc. Chem. Res. 2009, 42, 463
3. Multicomponent Reactions: Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005. For recent reviews about asymmetric multicomponent reactions (AMCRs) see
4. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156
5. Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
6. Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439
7. Kalinski, C.; Leomine, H.; Schmidt, J.; Burdack, C.; Kolb, J.; Umkehrer, M.; Ross, G. Synthesis 2008, 4007
8. Banfi, L.; Riva, R.; Basso, A. Synlett 2010, 23
9. Dömling, A. Chem. Rev. 2006, 106, 17
10. For a selected recent work, see: Pando, O.; Stark, S.; Denkert, A.; Porzel, A.; Preusentanz, R.; Wessjohann, L. A. J. Am. Chem. Soc. 2011, 133, 7692
11. Brioche, J.; Masson, G.; Zhu, J. Org. Lett. 2010, 12, 1432
12. Okandeji, B. O.; Sello, J. K. J. Org. Chem. 2009, 74, 5067
13. Leon, F.; Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1762
14. Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985
15. For a detailed mechanism of the Passerini reaction, see: Maeda, S.; Komagawa, S.; Uchiyama, M.; Morokuma, K. Angew. Chem., Int. Ed. 2011, 50, 644
16. Pando, O.; Stark, S.; Denkert, A.; Porzel, A.; Preusentanz, R.; Wessjohann, L. A. J. Am. Chem. Soc. 2011, 133, 7692
17. Scheffelaar, R.; Nijenhuis, R. A. K.; Paravidino, M.; Lutz, M.; Spek, A. L.; Ehlers, A. W.; de Kanter, F. J. J.; Groen, M. B.; Orru, R. V. A.; Ruijter, E. J. Org. Chem. 2009, 74, 660
18. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
19. Finn, M. G.; Fokin, V. V. Eds. Chem. Soc. Rev. 2010, 39, 1221
20. Wang, Q.; Hawker, C. Eds. Chem. Asian. J. 2011, 6, 2565
21. Meldal, M.; Christensen, C.; Tornøe, C. W. J. Org. Chem. 2002, 67, 3057
22. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
23. For a recent review on 1,2,3-triazoles as pharmacophores, see: Agalave, S. G.; Maujan, S. R.; Pore, V. S. Chem. Asian J. 2011, 6, 2696
24. Yakushiji, F.; Tanaka, H.; Muguruma, K.; Iwasashi, T.; Yamazaki, Y.; Hayashi, Y. Chem.-Eur. J. 2011, 17, 12587
25. Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674
26. Alcaide, B.; Almendros, P.; Quirós, T. Adv. Synth. Catal. 2011, 353, 585
27. Alcaide, B.; Almendros, P.; Carrascosa, R. Chem.-Eur. J. 2011, 17, 4968
28. Alcaide, B.; Almendros, P.; Cabrero, G.; Callejo, R.; Ruiz, M. P.; Arnó, M.; Domingo, L. R. Adv. Synth. Catal. 2010, 352, 1688
29. Alcaide, B.; Almendros, P.; Carrascosa, R.; Torres, M. R. Adv. Synth. Catal. 2010, 352, 1277
30. Alcaide, B.; Almendros, P.; Carrascosa, R.; Martinez del Campo, T. Chem.-Eur. J. 2010, 16, 13243
31. Singh, P.; Singh, P.; Kumar, M.; Gut, J.; Rosenthal, P. J.; Kumar, K.; Kumar, V.; Mahajan, M. P.; Bissety, K. Bioorg. Med. Chem. Lett. 2012, 22, 57
32. Singh, P.; Raj, R.; Kumar, V.; Mahajan, M. P.; Bedi, P. M. S.; Kaur, T.; Saxena, A. K. Eur. J. Med. Chem. 2012, 47, 594
33. Gavrilyuk, J. I.; Wuellner, U.; Barbas, C. F., III Bioorg. Med. Chem. Lett. 2009, 19, 1421
34. Vatmurge, N. S.; Hazra, B. G.; Pore, V. S.; Shirazi, F.; Chavan, P. S.; Desphande, M. V. Bioorg. Med. Chem. Lett. 2008, 18, 2043
35. Palomo, C.; Aizpurua, J. M.; Balentová, E.; Azcune, I.; Santos, J. I.; Jiménez-Barbero, J.; Cañada, J.; Miranda, J. I. Org. Lett. 2008, 10, 2227
36. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208
37. Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315
38. Shapiro, N.; Vigalok, A. Angew. Chem., Int. Ed. 2008, 47, 2849
39. Pirrung, M. C.; Sarma, K. D. J. Am. Chem. Soc. 2004, 126, 444
40. El Kaïm, L.; Grimaud, L. Mol. Divers. 2010, 14, 855
41. El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem. 2007, 72, 4169
42. El Kaïm, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 5021-5023
43. El Kaïm, L.; Grimaud, L.; Oble, J. Angew. Chem., Int. Ed. 2005, 44, 7961
44. Neu, H. C.; Fu, K. P. Antimicrob. Agents Chemother. 1979, 15, 209
45. Bebrone, C.; Lassaux, P.; Vercheval, L.; Sohier, J.-S.; Jehaes, A.; Sauvage, E.; Galleni, M. Drugs 2010, 70, 561
46. Drawz, S. M.; Bonomo, R. A. Clin. Microbiol. Rev. 2010, 23, 160
47. Long, D. D.; Aggen, J. B.; Christensen, B. G.; Judice, J. K.; Hegde, S. S.; Kaniga, K.; Krause, K. M.; Linsell, M. S.; Moran, E. J.; Pace, J. L. J. Antibiot. 2008, 61, 595
48. Vatmurge, N. S.; Hazra, B. G.; Pore, V. S.; Shirazi, F.; Deshpande, M. V.; Kadreppa, S.; Chattopadhyay, S.; Gonnade, R. G. Org. Biomol. Chem. 2008, 6, 3823
49. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gómez-Campillos, G. Eur. J. Org. Chem. 2011, 364
50. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem.-Eur. J. 2009, 15, 9987
51. Montenegro, H. E.; Ramírez-López, P.; de la Torre, M. C.; Asenjo, M.; Sierra, M. A. Chem.-Eur. J. 2010, 16, 3798
52. Özçubukçu, S.; Ozkal, E.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2009, 11, 4680
53. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853
54. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Cabrero, G.; Callejo, R.; Ruiz, M. P. Eur. J. Org. Chem. 2008, 4434
55. In contrast to the thermal Huisgen 1,3-cycloaddition which afford a mixture of 1,4 and 1,5-triazole regioisomers, CuAAC allows the synthesis of 1,4-disubstituted 1,2,3-triazoles regioselectively. See: Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
56. 2 (SHELXL-97). The nonhydrogen atoms were refined anisotropically. The hydrogen atoms were refined only in terms of their coordinates. CCDC-873490 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.cam.ac.uk/data-request/ cif.