New protocol for efficient N-chlorinations of amides and carbamates

Synthesis

Volumn , Issue 12, 2003, Pages 1916-1919

  Larionov, Oleg V ^a   Kozhushkov, Sergei I ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alumina; Amides; Amino acids; Calcium hypochlorite; N chlorination

Indexed keywords

AMINO ACIDS; CALCIUM COMPOUNDS; CHLORINATION; ESTERS;

AMIDES;

SYNTHESIS (CHEMICAL);

1 CHLOROHEXAHYDROAZEPIN 2 ONE; 1 CHLOROPYRROLIDIN 2 ONE; ACETIC ACID DERIVATIVE; ALUMINUM OXIDE; AMIDE; AMINO ACID DERIVATIVE; CALCIUM HYPOCHLORITE; CARBAMIC ACID DERIVATIVE; CYCLOPROPANE; HYPOCHLORITE; LACTAM; METHYL 1 (TERT BUTOXYCARBONYLCHLOROAMINO)CYCLOPROPANECARBOXYLATE; METHYL 2 (TERT BUTOXYCARBONYLCHLOROAMINO)CYCLOPROPANECARBOXYLATE; METHYL(BENZYLOXYCARBONYLCHLOROAMINO)CYCLOPROPYL ACETATE; METHYL(TERT BUTOXYCARBONYLCHLOROAMINO)CYCLOPROPYL ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0141742409     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41037     Document Type: Article

References (36)

1. (a) Part 95 in the series 'Cyclopropyl Building Blocks in Organic Synthesis'. For Part 94 see: Gensini, M.; de Meijere, A. Chem.-Eur. J. 2003, 9, in press
2. (b) Part 93: Kozhushkov, S. I.; Leonov, A.; de Meijere, A. Synthesis 2003, 956.
3. Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis; John Wiley and Sons: New York, 1967, 78.
4. Barton, D. R. H.; Ollis, W. D. In Comprehensive Organic Chemistry, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1979, 1030.
5. (a) Poisel, H.; Schmidt, U. Angew. Chem., Int. Ed. Engl. 1976, 15, 294.
6. (b) Poisel, H. Chem. Ber. 1977, 110, 948. (c) Kolar, A. J.; Olsen, R. K. Synthesis 1977, 457.
7. (c) Kolar, A. J.; Olsen, R. K. Synthesis 1977, 457.
8. Daoust, B.; Lessard, J. Tetrahedron 1999, 55, 3495.
9. (a) Kawaya, M.; Neogi, P.; Khattri, P. S.; Butsugan, Y. Chem. Lett. 1990, 577.
10. (b) Miosses, B.; Danion-Bougot, R.; Danion, D. Synthesis 1994, 1171.
11. (a) Caprara, G.; Lemetre, G.; Vercellone, A. Ann. Chim. (Rome) 1959, 49, 1167.
12. (b) Drago, R. S.; Went, D. A.; Carlson, R. J. J. Am. Chem. Soc. 1962, 84, 1106.
13. Bachand, C.; Driguez, H.; Paton, J. M.; Touchard, D.; Lessard, J. J. Org. Chem. 1974, 39, 3136.
14. Zimmer, H.; Audrieth, L. F. J. Am. Chem. Soc. 1954, 76, 3856.
15. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Tsadjout, A. Syntett 2000, 813.
16. (a) Hirano, M.; Yakabe, S.; Fukami, M.; Morimoto, T. Synth. Commun. 1997, 27, 2783.
17. (b) Hirano, M.; Yakabe, S.; Uraoka, N.; Morimoto, T. Org. Prep. Proced. Int. 1998, 30, 360.
18. Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimoto, T. Synthesis 1997, 1161.
19. Larionov, O. V.; de Meijere, A. manuscript in preparation.
20. N-chlorination of the cyclopropyl-containing amino acid derivatives 1-H and 2-H with any of the other known reagents was to a greater extent hampered by some side-processes furnishing the products 1-Cl and 2-Cl respectively in low yields and purities.
21. (a) Moist alumina was prepared according to the published procedure: Greenhalgh, R. P. Synlett 1992, 235.
22. (b) For a recent review on reactions carried out on alumina see: Kabalka, G. W.; Pagni, R. M. Tetrahedron 1997, 53, 7999.
23. Larionov, O. V. Part of a forthcoming Dissertation, University of Göttingen 2004.
24. Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. 1 1998, 2485.
25. Kordes, M.; Winsel, H.; de Meijere, A. Eur. J. Org. Chem. 2000, 3235.
26. Csuk, R.; von Scholz, Y. Tetrahedron 1994, 50, 10431.
27. l2) of the previously described 3-(trans-2-nitrocyclopropyl)alanine: Larionov, O. V.; Savel'eva, T. F.; Kochetkov, K. A.; Ikonnikov, N. S.; Kozhushkov, S. I.; Yufit, D. S.; Howard, J. A. K.; Khrustalev, V. N.; Belokon, Yu. N.; de Meijere, A. Eur. J. Org. Chem. 2003, 5, 869.
28. Yokoyama, Y.; Hikawa, H.; Murakami, Y. J. Chem. Soc., Perkin Trans. 1 2001, 1431.
29. (a) Phan, X. T.; Shannon, P. J. J. Org. Chem. 1983, 48, 5164.
30. (b) Beyer, H.; Korosi, J. Chem. Ber. 1961, 94, 480.
31. For the preparation and application of this compound in chemical industry see: (a) Walles, W. E. US Patent 3591601, 1971; Chem. Abstr. 1971, 75, 88620. (b) Choi, S. K. US Patent 3875147, 1975; Chem. Abstr. 1975, 83, 79999. (c) Walles, W. E. US Patent 3850920, 1974; Chem. Abstr. 1975, 82, 125410.
32. For the preparation and application of this compound in chemical industry see: (a) Walles, W. E. US Patent 3591601, 1971; Chem. Abstr. 1971, 75, 88620. (b) Choi, S. K. US Patent 3875147, 1975; Chem. Abstr. 1975, 83, 79999. (c) Walles, W. E. US Patent 3850920, 1974; Chem. Abstr. 1975, 82, 125410.
33. For the preparation and application of this compound in chemical industry see: (a) Walles, W. E. US Patent 3591601, 1971; Chem. Abstr. 1971, 75, 88620. (b) Choi, S. K. US Patent 3875147, 1975; Chem. Abstr. 1975, 83, 79999. (c) Walles, W. E. US Patent 3850920, 1974; Chem. Abstr. 1975, 82, 125410.
34. For the preparation and application of this compound in chemical industry see: (a) Lessard, J.; Couture, Y.; Mondon, M.; Touchard, D. Can. J. Chem. 1984, 62, 105. (b) Phan, X. T.; Shannon, P. J. J. Org. Chem. 1983, 48, 5164. (c) See ref. 23a,c.
35. For the preparation and application of this compound in chemical industry see: (a) Lessard, J.; Couture, Y.; Mondon, M.; Touchard, D. Can. J. Chem. 1984, 62, 105. (b) Phan, X. T.; Shannon, P. J. J. Org. Chem. 1983, 48, 5164. (c) See ref. 23a,c.
36. For the preparation and application of this compound in chemical industry see: (a) Lessard, J.; Couture, Y.; Mondon, M.; Touchard, D. Can. J. Chem. 1984, 62, 105. (b) Phan, X. T.; Shannon, P. J. J. Org. Chem. 1983, 48, 5164. (c) See ref. 23a,c.