Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides

Synthetic Communications

Volumn 43, Issue 16, 2013, Pages 2155-2164

  Goodman, Cassie A ^a   Eagles, Joel B ^a   Rudahindwa, Leandre ^a   Hamaker, Christopher G ^a   Hitchcock, Shawn R ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

Acyl transfer; Aminolysis; N acyl succinimide; N carbamoyl succinimide

Indexed keywords

1,2 DICHLOROETHANE; AROMATIC AMINE; CARBOXYLIC ACID DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ACYLATION; ARTICLE; CRYSTAL STRUCTURE; HYDROLYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84879082397     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2012.690061     Document Type: Article

References (40)

1. Wuts, P. G. M.; Greene, T. W. Green's Protective Groups in Organic Synthesis, 4th ed.; Wiley and Sons: New York, 2007; Chap. 7, p. 773-802.
2. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 6th ed.; Wiley and Sons: New York, 2007; Chap. 16, pp. 1427-1439.
3. Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H.; Himes, R. H. Bioorg. Medi. Chem. Lett. 1994, 4, 335-338
4. Woodward, R. B.; Doering, W. E. J. Am. Chem. Soc. 1945, 67, 860-874
5. Baumann, E. Ber. Dtsch. Chem. Ges. 1886, 19, 3218-3222
6. Schotten, C. Ber. Dtsch. Chem. Ges. 1884, 17, 2544-2547.
7. Zhu, J.; Razler, T. M.; Xu, Z.; Conlon, D. A.; Sortore, E. W.; Fritz, A. W.; Demerzhan, R.; Sweeney, J. T. Org. Process Res. Dev. 2011, 15, 438-442
8. Hajiwara, D.; Miyake, H.; Igari, N.; Karino, M.; Maeda, Y.; Fujii, T.; Matsuo, M. J. Med. Chem. 1994, 37, 2090-2099
9. Sheehan, J. C.; Preston, J.; Cruickshank, P. A. J. Am. Chem. Soc. 1965, 87, 2492-2493
10. Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067-1068.
11. Carpino, L. A.; El-Faham, A.; Albericio, F. J. Org. Chem. 1995, 60, 3561-3564
12. Konig, W.; Geiger, R. Ber. Dtsch. Chem. Ges. 1970, 103, 788-798
13. Konig, W.; Geiger, R. Ber. Dtsch. Chem. Ges. 1970, 103, 2024-2033.
14. Wu, X.; Ling, C.-C.; Bundle, D. R. Org. Lett. 2004, 6, 4407-4410
15. Lucente, G.; Romeo, A. Chem. Comm. 1971, 1605-1607
16. Bodansky, M.; du Vigneaud, V. J. Am. Chem. Soc., 1959, 81(21), 5688-5691.
17. Kessler, D.; Roth, P. J.; Theato, P. Langmuir 2009, 25, 10068-10076.
18. Feldman, K. S.; Sambandam, A.; Bowers, K. E.; Appel, H. M. J. Org. Chem. 1999, 64, 5794-5803
19. Pless, J.; Boissonnas, R. A. Helv. Chim. Acta 1963, 46, 1609-1625
20. Guttman, S.; Boissonnas, R. A. Helv. Chim. Acta 1963, 46, 1626-1637.
21. Lockett, M. R.; Phillips, M. F.; Jarecki, J. L.; Peelen, D.; Smith, L. M. Langmuir, 2008, 24, 69-75
22. Anderson, J. W.; Zimmerman, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1964, 86, 1839-1842.
23. Larrive-Aboussafy, C.; Jones, B. P.; Price, K. E.; Hardink, M. A.; McLaughlin, R. W.; Lillie, B. M.; Hawkins, J. M.; Vaidyanathan, R. Org. Lett. 2010, 12, 324-327.
24. Katritzky, A. R.; Fedoseyenko, D.; Kim, M. S.; Steel, P. J. Tetrahedron: Asymmetry 2010, 21, 51-57
25. Yang, X.; Birman, V. B. Org. Lett. 2009, 11, 1499-1502.
26. Taaning, R. H.; Lindsay, K. B.; Schiott, B.; Daasbjerg, K.; Skrydstrup, T. J. Am. Chem. Soc. 2009, 131, 10253-1026
27. Boyd, H.; Calder, I. C.; Leach, S. J.; Milligan, B. Int. J. Peptide Protein Res. 1972, 4, 109-115
28. Boyd, H.; Leach, S. H.; Milligan, B. Int. J. Peptide Protein Res. 1972, 4, 117-122
29. McAlees, A. J.; McCrindle, R. J. Chem. Soc. C 1969, 2425-2435
30. Djerassi, C.; Lenk, C. T. J. Am. Chem. Soc. 1953, 75, 3493-3495
31. Heller, G.; Jacobsohn, P. Chem. Ber. 1921, 54, 1107-1117
32. Titherley, A. W. J. Chem. Soc., Trans. 1904, 85, 1673-1691
33. Tafel, J.; Stern, M. Chem. Ber. 1900, 33, 2224-2236.
34. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Cryst. 2008, 41, 466.
35. Yokomatsu, T.; Arakawa, A.; Shibuya, S. J. Org. Chem. 1994, 59, 3506-3508.
36. CAD4Express Software; Enraf-Nonius, Delft, the Netherlands, 1994.
37. Harms, K.; Wocadlo, S. XCAD-4 program for processing CAD-4 diffractometer data; University of Marburg, Germany, 1995.
38. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
39. Sheldrick, G. M. SHELX 97, program for crystal structure refinement; University of Göttingen, Germany, 1997.
40. Lee, S. Y.; Lee, C. W.; Oh, D. Y. J. Org. Chem. 1999, 64, 7017-7022.