Reaction of γ-hydroy-N-[1-(dimethylcarbamoyl)ethyl]butanamides under the 'direct amide cyclization' conditions

Helvetica Chimica Acta

Volumn 89, Issue 1, 2006, Pages 153-175

  Iliev, Boyan ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BUTANE; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

BUTANAMIDES; DIRECT AMIDE CYCLIZATION (DAC); HYDROXY ACIDS; OXAZOLONE;

NITROGEN COMPOUNDS;

2 [(3,4,4 TRIMETHYLTETRAHYDROFURAN 2 YLIDEN)AMINO] 2 METHYLPROPANOIC ACID; 2 [(3,4,4,4 TETRAMETHYLTETRAHYDROFURAN 2 YLIDEN)AMINO] 2 METHYLPROPANOIC ACID; 2 [(4 CHLORO 3,3 DIMETHYLBUTANOYL)AMINO] 2 METHYLPROPANOIC ACID; 2 [(4 CHLOROBUTANOYL)AMINO] 2 METHYLPROPANOIC ACID; 2 [(4,4 DIMETHYLTETRAHYDROFURAN 2 YLIDEN)AMINO] 2 METHYLPROPANOIC ACID; 2 METHYL N [1 METHYL 1 (N METHYL N PHENYLCARBAMOYL)ETHYL] 2 [(2,3,4,5 TETRAHYDRO 4,4 DIMETHYLFURAN 2 YLIDEN)AMINO]PROPANAMIDE; 2H AZIRIN 3 AMINE; AMIDE; AZIRINE DERIVATIVE; CHLORINE DERIVATIVE; CYCLODEPSIPEPTIDE; GAMMA HYDROXY N [1 (DIMETHYLCARBAMOYL)ETHYL]BUTANAMIDE; HYDROCHLORIC ACID; HYDROXYACID; LACTONE DERIVATIVE; OXAZOLONE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 31344474201     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690008     Document Type: Article

References (46)

1. C. E. Ballard, H. Yu, B. Wang, Curr. Med. Chem. 2002, 9, 471.
2. J. S. Davies, J. Peptide Sci. 2003, 9, 471.
3. T. G. Back, Tetrahedron 1997, 33, 3041.
4. A. Yurek-George, F. Habens, M. Brimmell, G. Packham, A. Ganesan, J. Am. Chem. Soc. 2004, 126, 1030.
5. C. Palomo, M. Oiarbide, J. Garcia, A. Gonzalez, R. Razos, J. Ordiozola, P. Banuelos, M. Tello, A. Linden, J. Org. Chem. 2004, 69, 4126.
6. F. Sarabia, S. Chammaa, F. Lopez-Herrera, Tetrahedron Lett. 2002, 43, 2961.
7. W. L. Duax, J. F. Griffin, D. A. Langs, G. D. Smith, Biopolymers, 1996, 40, 141.
8. P. Vongvilai, M. Isaka, P. Kittakoop, P. Srikitikulchai, P. Kongsaeree, S. Prabpai, Y. Thebtaranonth, Helv. Chim. Acta 2004, 87, 2066.
9. A. B. Mauger, Top. Antibiot. Chem. 1980, 5, 223.
10. D. Obrecht, H. Heimgartner, Tetrahedron Lett. 1983, 24, 1921.
11. D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1987, 70, 329.
12. D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1984, 67, 526.
13. J. E. F. Magirius, Ph.D. Thesis, University of Zurich, 1995.
14. K. N. Koch, A. Linden, H. Heimgartner, Tetrahedron 2001, 57, 2311.
15. P. Köttgen, planned Ph.D. Thesis, University of Zurich.
16. B. Iliev, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 3215.
17. B. Iliev, A. Linden, H. Heimgartner, Tetrahedron, in press.
18. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13.
19. R. Miller, W. Theis, G. Heilig, S. Kirchmeyer, J. Org. Chem. 1991, 56, 1453.
20. B. Travis, R. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824.
21. J. M. Schomaker, B. R. Travis, B. Borhan, Org. Lett. 2003, 5, 3089.
22. D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1990, 73, 221.
23. H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
24. C. K. Johnson, 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
25. J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
26. T. Joseph, J. Tam, M. Kitadani, Y. L. Chow, Can. J. Chem. 1976, 54, 3517.
27. S. Richard, G. Prie, A. Guignard, J. Thibonet, J. Luc Parrain, A. Duchene, M. Abarbri, Helv. Chim. Acta 2003, 86, 726.
28. R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 105, 1080.
29. M. Noack, R. Goettlich, Eur. J. Org. Chem. 2002, 3171.
30. J. Iqbal, R. Srivastava, Tetrahedron 1991, 47, 3155.
31. S. Murahashi, Y. Makabe, K. Kunita, J. Org. Chem. 1988, 53, 4489.
32. K. Brannock, R. Burpitt, J. Am. Chem. Soc. 1961, 83, 3576.
33. J. Mihelcic, K. Moeller, J. Am. Chem. Soc. 2003, 125, 36.
34. E. Lee, C. Yoon, T. Lee, S. Kim, T. Ha, Y. Sung, S. Park, S. Lee, J. Am. Chem. Soc. 1998, 120, 7469.
35. J. P. Gouesnard, Bull. Soc. Chim. Fr. 1989, 88.
36. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
37. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
38. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
39. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
40. A. L. Spek, PLATON, J. Appl. Crystallogr. 2003, 36, 7.
41. E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477.
42. D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.6.8, p. 219.
43. D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, p. 200.
44. R. F. Steward, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
45. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
46. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.