Synthesis of functionalized β-lactams and pyrrolidine-2,5-diones through a metal-free sequential ugi-4CR/cyclization reaction

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 7926-7934

  Ghabraie, Elmira ^a   Balalaie, Saeed ^a,b   Mehrparvar, Saber ^a   Rominger, Frank ^c  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES;

BETA-LACTAMS; DIVERSITY-ORIENTED SYNTHESIS; FUNCTIONALIZED; HIGH YIELD; METAL FREE; PYRROLIDINES; SHORT REACTION TIME;

SYNTHESIS (CHEMICAL);

3 BENZYL IDENE N CYCLOHEXYL 4 OXO 1 PHENYL 2 [4 (TRIFLUOROMETHYL)PHENYL]AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE 1 (4 BROMOPHENYL) N (TERT BUTYL) 4 OXO 2 PHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 1 (4 ISOPROPYLPHENYL) 4 OXO 2 PHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 2 (3 NITROPHENYL) 4 OXO 1 PHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 2 (4 CHLOROPHENYL) 4 OXO 1 PHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 2 (4 CYANOPHENYL) 4 OXO 1 PHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1 PHENYL 2 (3,4,5 TRIMETHOXYPHENYL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1 PHENYL 2 (4 (TRIFLUOROMETHYL)PHENYL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1 PHENYL 2 (PYRIDIN 2 YL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1 PHENYL 2 (PYRIDIN 3 YL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1 PHENYL 2 (THIOPHEN 2 YL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N (TERT BUTYL) 4 OXO 1,2 DIPHENYLAZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N CYCLOHEXYL 4 OXO 1 PHENYL 2 (P TOLYL)AZETIDINE 2 CARBOXAMIDE; 3 BENZYLIDENE N CYCLOHEXYL 4 OXO 1,2 DIPHENYLAZETIDINE 2 CARBOXAMIDE; 4 (4 BENZYLIDENE 1 (TERT BUTYL) 2,5 DIOXO 3 (PHENYLAMINO)PYRROLIDIN 3 YL)BENZONITRILE; 4 (4 BENZYLIDENE 1 CYCLOHEXYL 2,5 DIOXO 3 (PHENYLAMINO)PYRROLIDIN 3 YL)BENZONITRILE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 (4 CHLOROPHENYL) 3 (PHENYLAMINO)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 (PHENYLAMINO) 3 (4 TRIFLUOROMETHYL)PHENYL)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 (PHENYLAMINO) 3 (P TOLYL)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 (PHENYLAMINO) 3 (PYRIDIN 3 YL)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 PHENYL 3 (PHENYLAMINO) PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 (TERT BUTYL) 3 [(3,4 DIMETHYLPHENYL)AMINO] 3 PHENYLPYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 CYCLOHEXYL 3 (4 METHOXYPHENYL) 3 (PHENYLAMINO)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 CYCLOHEXYL 3 (PHENYLAMINO) 3 (4 (TRIFLUOROMETHYL)PHENYL)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 1 CYCLOHEXYL 3 PHENYL 3 (PHENYLAMINO)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 3 (4 BROMOPHENYL) 1 CYCLOHEXYL 3 (PHENYLAMINO)PYRROLIDINE 2,5 DIONE; 4 BENZYLIDENE 3 (4 CHLOROPHENYL) 1 CYCLOHEXYL 3 (PHENYLAMINO)PYRROLIDINE 2,5 DIONE; BETA LACTAM DERIVATIVE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; 2 PYRROLIDONE DERIVATIVE; BETA LACTAM; METAL;

ARTICLE; COMBINATORIAL CHEMISTRY; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; THIN LAYER CHROMATOGRAPHY; UGI 4CR CYCLIZATION; CHEMISTRY; PROCEDURES; STEREOISOMERISM; SYNTHESIS;

BETA-LACTAMS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; METALS; PYRROLIDINONES; STEREOISOMERISM;

EID: 84923881521     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5010422     Document Type: Article

References (73)

1. Müller, T. J. J. Multicomponent Reactions, Science of Synthesis; Georg Thieme: Stuttgart, Germany, 2014.
2. Domling, A. Chem. Rev. 2006, 106, 17
3. Zhu, J.; Bienaymé, H.; Multicomponent reactions; Wiley-VCH: Weinheim, Germany, 2005,.
4. Domling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083
5. Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234
6. Isambert, N.; Lavilla, R. Chem. Eur. J. 2008, 14, 8444
7. Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471
8. Hulme, C.; Gore, V. Curr.Med.Chem. 2003, 10, 51
9. Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321
10. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168
11. Ugi, I. Angew. Chem., Int. Ed. 1982, 21, 810
12. Ugi, I.; Streinbrückner, C. Chem. Ber. 1961, 94, 734
13. Zhang, L.; Zhao, F.; Zheng, M.; Zhai, Y.; Liu, H. Chem. Commun. 2013, 49, 2894
14. Zhang, L.; Zhao, F.; Zheng, M.; Zhai, Y.; Wang, J.; Liu, H. Eur. J. Org. Chem. 2013, 5710
15. Sinha, M. K.; Khoury, K.; Herdtweckb, E.; Dömling, A. Org. Biomol. Chem. 2013, 11, 4792
16. Jida, M.; Betti, C.; Urbanczyk-Lipkowska, Z.; Tourwé, D.; Ballet, S. Org. Lett. 2013, 15, 5866
17. Che, C.; Li, S.; Jiang, X.; Quan, J.; Lin, S.; Yang, Z. Org. Lett. 2010, 12, 4682
18. Che, C.; Yang, B.; Jiang, X.; Shao, T.; Yu, Z.; Tao, C.; Li, S.; Lin, S. J. Org. Chem. 2014, 79, 436
19. Che, C.; Li, S.; Yu, Z.; Li, F.; Xin, S.; Zhou, L.; Lin, S.; Yang, Z. Comb. Sci. 2014, 15, 202
20. Dietrich, S. A.; Banfi, L.; Basso, A.; Damonte, G.; Guanti, G.; Riva, R. Org. Biomol. Chem. 2005, 3, 97
21. Riva, R.; Banfi, L.; Basso, A.; Cerulli, V.; Guanti, G.; Pani, M. J. Org. Chem. 2010, 75, 5134
22. Hulme, C.; Peng, J.; Tang, S.-Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021
23. Banfi, L.; Basso, A.; Riva, R. In Synthesis of Heterocycles via Multicomponent Reactions I; Orru, R. V. A.; Ruijter, E., Eds.; Springer: Heidelberg, Germany, 2010; pp 1-40.
24. Santra, S.; Andreana, P. R. J. Org. Chem. 2011, 76, 2261
25. Santra, S.; Andreana, P. R. Angew. Chem., Int. Ed. 2011, 50, 9418
26. Hay, L. A.; Koenig, T. M.; Gina, F. O.; Copp, J. D.; Mitcel, D. J. Org. Chem. 1998, 63, 5050
27. Yanada, R.; Obika, S.; Oyama, M.; Takemoto, Y. Org. Lett. 2004, 6, 2825
28. Yanada, R.; Obika, S.; Inokuma, T.; Yanada, K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem. 2005, 70, 6972
29. Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741
30. Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett. 2006, 8, 4927
31. Dai, W. M.; Shi, J.; Wu, J. Synlett 2008, 2716
32. Vieth, M.; Cummins, D. J. J. Med. Chem. 2000, 43, 3020
33. Yanada, R.; Obika, S.; Kobayashi, Y.; Inokuma, T.; Oyama, M.; Yanada, K.; Takemoto, Y. Adv. Synth. Catal. 2005, 347, 1632
34. Arthuis, M.; Pontikis, R.; Florent, J.-C. Tetrahedron Lett. 2007, 48, 6397
35. Mag, L. A.; Koenig, T. M.; Ginah, F. O.; Copp, J. D.; Mitchel, D. J. Org. Chem. 1998, 63, 5050
36. Plastina, P.; Salerno, G.; Mancuso, R. Synthesis 2006, 4247
37. Patra, R.; Maiti, S. B.; Chatterjee, A.; Chakravarty, A. K. Tetrahedron Lett. 1991, 32, 1363
38. Kraft, M. E.; Romero, R. H.; Scott, I. L. J. Org. Chem. 1992, 5, 5277
39. Krafft, M. E.; Wright, J. A.; Bonaga, L. V. R. Can. J. Chem. 2005, 83, 1006
40. Bararjanian, M.; Balalaie, S.; Rominger, F.; Movassagh, B.; Bijanzadeh, H. R. J. Org. Chem. 2010, 75, 2806
41. Bararjanian, M.; Balalaie, S.; Movassagh, B.; Bijanzadeh, H. R. Tetrahedron Lett. 2010, 51, 3277
42. Bararjanian, M.; Hosseinzadeh, S.; Balalaie, S.; Bijanzadeh, H. R. Tetrahedron 2011, 67, 2644
43. Bararjanian, M.; Balalaie, S.; Rominger, F.; Movassagh, B.; Bijanzadeh, H. R. Mol. Divers. 2011, 15, 583
44. Bararjanian, M.; Hosseinzadeh, S.; Balalaie, S.; Bijanzadeh, H. R.; Wolf, E. Tetrahedron Lett. 2011, 52, 3329
45. Balalaie, S.; Motaghedi, H.; Bararjanian, M.; Tahmassebi, D.; Bijanzadeh, H. R. Tetrahedron 2011, 67, 9134
46. Balalaie, S.; Motaghedi, H.; Tahmassebi, D.; Bararjanian, M.; Bijanzadeh, H. R. Tetrahedron Lett. 2012, 53, 6177
47. Maghari, S.; Ramezanpour, S.; Balalaie, S.; Darvish, F.; Rominger, F.; Bijanzadeh, H. R. J. Org. Chem. 2013, 78, 6450
48. Kumar, A.; Vachhani, D. D.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Beilstein J. Org. Chem. 2013, 9, 2097
49. Kumar, A.; Vachhani, D. D.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Eur. J. Org. Chem. 2013, 2288
50. Modha, S. G.; Kumar, A.; Vachhani, D. D.; Jacobs, J.; Sharma, S. K.; Parmar, V. S.; Meervelt, L. V.; Van der Eycken, E. V. Angew. Chem., Int. Ed. 2012, 51, 9572
51. Modha, S. G.; Vachhani, D. D.; Jacobs, J.; Meerveltb, L. V.; Van der Eycken, E. V. Chem. Commun. 2012, 48, 6550
52. Modha, S. G.; Kumar, A.; Vachhani, D. D.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Chem. Commun. 2012, 48, 10916
53. Kumar, A.; Li, Z.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Chem. Commun. 2013, 49, 6803
54. Vachhani, D. D.; Galli, M.; Jacobs, J.; Meerveltb, L. V.; Van der Eycken, E. V. Chem. Commun. 2013, 49, 7171
55. Kumar, A.; Li, Z.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Org. Lett. 2013, 15, 1874
56. Vachhani, D. D.; Kumar, A.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Eur. J. Org. Chem. 2013, 1223
57. Alcaide, B.; Almendros, P. Acc. Chem. Res. 2014, 47, 939 and references cited therein
58. Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526 and references cited therein
59. Parsons, A. F. Tetrahedron 1996, 52, 4149
60. Konno, K.; Shirihama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939
61. Konno, K.; Hashimoto, K.; Ohfune, Y.; Shirihama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 110, 4807
62. Garst, M. E.; Dolby, L. J.; Esfandiari, S.; Fedoruk, N. C.; Chamberlain, N. C.; Avey, A. A. J. Org. Chem. 2000, 65, 7098
63. Fisher, J. F.; Meroveh, S. O.; Mobashery, S. Chem. Rev. 2005, 105, 395
64. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437
65. Szostak, M.; Aubé, J. Chem. Rev. 2013, 113, 5701
66. Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 10.1021/cr4005549
67. Leadbeater, N. E.; Marco, M.; Tominack, B. J. Org. Lett. 2003, 5, 3919
68. Leadbeater, N. E.; Marco, M. Angew. Chem., Int. Ed. 2003, 42, 1407
69. Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin, V. V. Org. Lett. 2010, 12, 4217
70. Rueping, M.; Parra, A. Org. Lett. 2010, 12, 5281
71. Thomé, I.; Bolm, C. Org. Lett. 2012, 14, 1892
72. Bossi, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R. Tetrahedron Lett. 1997, 38, 2519
73. Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 3633