Synthesis of functionalized pseudopeptides through five-component sequential Ugi/nucleophilic reaction of N-substituted 2-alkynamides with hydrazides

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6450-6456

  Maghari, Shokoofeh ^a   Ramezanpour, Sorour ^a   Balalaie, Saeed ^a   Darvish, Fatemeh ^a   Rominger, Frank ^b   Bijanzadeh, Hamid Reza ^a,c  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF HEIDELBERG   (Germany)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; FUNCTIONALIZED; ISOCYANIDES; POLYFUNCTIONAL; PRIMARY AMINES; PROPIOLIC ACID; PSEUDOPEPTIDES;

ADDITION REACTIONS; SUBSTITUTION REACTIONS;

REACTION INTERMEDIATES;

ALDEHYDE DERIVATIVE; AMINE; HYDRAZIDE DERIVATIVE; PSEUDOPEPTIDE; ALDEHYDE; ALKYNE; AMIDE; CYANIDE; HYDRAZINE DERIVATIVE; PEPTIDE; PROPIOLIC ACID; PROPIONIC ACID DERIVATIVE;

ADDITION REACTION; ARTICLE; EVAPORATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TAUTOMERIZATION; CHEMICAL STRUCTURE; CHEMISTRY;

ALDEHYDES; ALKYNES; AMIDES; AMINES; CYANIDES; HYDRAZINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROPIONATES;

EID: 84880010727     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4003294     Document Type: Article

References (48)

1. Dömling, A. In Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Weinheim, 2005; p 76-94.
2. Slobbe, P.; Ruijler, E.; Orru, R. V. A. Med. Chem. Commun 2012, 3, 1189-1218
3. Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234-6246
4. Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083-3155
5. Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047-1050
6. Banfi, L.; Basso, A.; Guanti, G.; Kielland, N.; Repetto, C.; Riva, R. J. Org. Chem. 2007, 72, 2151-2160
7. Erb, W.; Neuville, L.; Zhu, J. J. Org. Chem. 2009, 74, 3109-3115
8. Corres, N.; Delgado, J. J.; García-Valverde, M.; Marcaccini, S.; Rodríguez, T.; Rojo, J.; Torroba, T. Tetrahedron 2008, 64, 2225-2232
9. Bararjanian, M.; Balalaie, S.; Rominger, F.; Movassagh, B.; Bijanzadeh, H. R. J. Org. Chem. 2010, 75, 2806-2812
10. Bararjanian, M.; Balalaie, S.; Rominger, F.; Movassagh, B.; Bijanzadeh, H. R. Mol. Divers. 2011, 15, 583-594
11. Barajanian, M.; Balalaie, S.; Movassagh, B.; Bijanzadeh, H. R. Tetrahedron Lett. 2010, 51, 3277-3279
12. Hartung, C. G.; Breindl, C.; Tillack, A.; Beller, M. Tetrahedron 2000, 56, 5157-5162
13. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547
14. Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541-2543
15. Müller, T. E. Tetrahedron Lett. 1998, 39, 5961-5962
16. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704
17. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160
18. Panda, N.; Raghavender, M. J. Org. Chem. 2012, 77, 9407-9412
19. Patil, N. T.; Kavthe, R. D.; Shinde, V. S. Tetrahedron 2012, 68, 8079-8146
20. Dabb, S. L.; Messerle, B. A. Dalton Trans. 2008, 6368-6371
21. Zhao, J.; Zheng, Z.; Bottle, S.; Chou, A.; Sarina, S.; Zhu, H. Chem. Commun 2013, 49, 2676-2678
22. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114
23. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398
24. Datta, S.; Roesky, P. W.; Blechert, S. Organometallics 2007, 26, 4392-4394
25. Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042-2043
26. Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343
27. Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570-4571
28. Jones, G. C.; Beard, W. Q.; Hauser, C. R. J. Org. Chem. 1963, 28, 199-203
29. Dabb, S. L.; Ho, J. H. H.; Hodgson, R.; Messerle, B. A.; Wagler, J. Dalton Trans. 2009, 634-642
30. Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3225
31. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771
32. Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772
33. Straub, T.; Haskel, A.; Neyroud, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017-5035
34. Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775
35. Straub, T.; Frank, W.; Reiss, G. J.; Eisen, M. S. Dalton Trans. 1996, 2541-2546
36. Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308
37. Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924
38. Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391
39. Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 2003, 935-946
40. Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967-3969
41. Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013
42. Sweeney, Z. K.; Salsman, J. L.; Andersen, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343
43. Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414
44. Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763
45. Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719
46. Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853-2856
47. Sheldrick, G. M. Bruker Analytical X-ray-Division, Madison, WI, 2008.
48. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122