A new entry into cis-3-amino-2-methylpyrrolidines via ring expansion of 2-(2-hydroxyethyl)-3-methylaziridines

Organic and Biomolecular Chemistry

Volumn 7, Issue 1, 2009, Pages 135-141

  D'Hooghe, Matthias ^a   Aelterman, Wim ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AROYLATION; AZIRIDINIUM SALTS; DE PROTECTIONS; FORMAL SYNTHESES; HIGH YIELDS; METHYLPYRROLIDINE; NUCLEOPHILIC DISPLACEMENTS; RING CLOSURES; RING EXPANSIONS;

AMINATION; AMINES;

COMPUTER NETWORKS;

AZIRIDINE DERIVATIVE; BENZAMIDE DERIVATIVE; EMONAPRIDE; NEUROLEPTIC AGENT; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG DESIGN; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTIPSYCHOTIC AGENTS; AZIRIDINES; BENZAMIDES; CHEMISTRY, ORGANIC; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM;

EID: 57549104191     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b816617j     Document Type: Article

References (34)

1. D. Bouzard P. Di Cesare M. Essiz J. P. Jacquet B. Ledoussal P. Remuzon R. E. Kessler J. Fung-Tomc J. Med. Chem. 1992 35 518
2. M. Takamatsu M. Matsui Y. Ikeda Eur. Pat. Appl. 1989
3. M. Takamatsu M. Matsui Y. Ikeda Chem. Abstr. 1990 113 71314
4. Y. Ito, H. Kato, S. Yasuda, N. Kato, T. Yoshida, and Y. Yamamoto, Jpn. Kokai Tokkyo Koho 1994, JP 06016624 A; Chem. Abstr., 1994, 121, 9155
5. K. Nakada, S. Kashimoto, M. Tajima, T. Ooe, K. Chiba, and K. Shibamori, Jpn. Kokai Tokkyo Koho 1996, JP 08073460 A; Chem. Abstr., 1996, 125, 58488
6. Y. Tsuzuki K. Tomita K. Shibamori Y. Sato S. Kashimoto K. Chiba J. Med. Chem. 2004 47 2097
7. M. Atanasova S. Ilieva B. Galabov Eur. J. Med. Chem. 2007 42 1184
8. S. Iwanami M. Takashima Y. Hirata O. Hasegawa S. Usada J. Med. Chem. 1981 24 1224
9. J. Ohmori K. Maeno K. Hidaka K. Nakato S. Sakamoto S.-i. Tsukamoto PCT Int. Appl. 1995
10. J. Ohmori K. Maeno K. Hidaka K. Nakato S. Sakamoto S.-i. Tsukamoto Chem. Abstr. 1995 123 285754
11. C. J. Andres P. H. Lee T. H. Nguyen A. I. Meyers J. Org. Chem. 1995 60 3189
12. P. Q. Huang S. L. Wang H. Zheng X. S. Fei Tetrahedron Lett. 1997 38 271
13. P. Q. Huang S. L. Wang J. L. Ye Y. P. Ruan Y. Q. Huang H. Zheng J. X. Gao Tetrahedron 1998 54 12547
14. N. Baricordi S. Benetti G. Biondini C. De Risi G. P. Pollini Tetrahedron Lett. 2004 45 1373
15. N. De Kimpe R. Verhé L. De Buyck L. Moens N. Schamp Synthesis 1982 43
16. N. De Kimpe P. Sulmon N. Schamp Angew. Chem. Int. Ed. 1985 24 88
17. W. Van Brabandt R. Van Landeghem N. De Kimpe Org. Lett. 2006 8 1105
18. N. De Kimpe W. Aelterman K. De Geyter J.-P. Declercq J. Org. Chem. 1997 62 5138
19. E. R. Buchman J. Am. Chem. Soc. 1936 58 1803
20. N. De Kimpe L. Moens Tetrahedron 1990 46 2965
21. D. W. Old D. T. Dinh PCT Int. Appl. 2007
22. D. W. Old D. T. Dinh Chem. Abstr. 2007 148 33531
23. D. W. Old and D. T. Dinh, U.S. Pat. Appl. Publ. 2008, US 2008033023 A1; D. W. Old, and D. T. Dinh, Chem. Abstr., 2008, 148, 222012
24. T. Rosen S. W. Fesik D. T. W. Chu A. G. Pernet Synthesis 1988 40
25. M. A. Williams H. Rappoport J. Org. Chem. 1994 59 3616
26. G. Giardina G. Dondio M. Grugni Synlett 1995 55
27. P. Di Cesare D. Bouzard M. Essiz J. P. Jacquet B. Ledoussal J. R. Kiechel P. Remuzon R. E. Kessler J. Fung-Tomc J. Desiderio J. Med. Chem. 1992 35 4205
28. J. K. Thottathil J. L. Moniot Tetrahedron Lett. 1986 27 151
29. K. Hashimoto H. Shirahama Tetrahedron Lett. 1991 32 2625
30. T. R. Webb C. Eigenbrot J. Org. Chem. 1991 56 3009
31. P. Gmeiner F. Orecher C. Thomas K. Weber Tetrahedron Lett. 1995 36 381
32. C. Gallina C. Marta C. Colombo A. Romeo Tetrahedron 1971 27 4681
33. H. Beierbeck J. K. Saunders Can. J. Chem. 1980 58 1258
34. J. K. Whitesell T. Lacour R. Lovell J. Pojman P. Ryan A. Yamada-Nosaka J. Am. Chem. Soc. 1988 110 991